Cas no 345223-64-5 (4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)-)

4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)- structure
345223-64-5 structure
Product Name:4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)-
CAS No:345223-64-5
MF:C12H21NO2
MW:211.30064368248
CID:2943216
Update Time:2022-07-26

4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)- Chemical and Physical Properties

Names and Identifiers

    • 4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)-
    • Inchi： 1S/C12H21NO2/c1-4-10-8-13-6-5-11(10)7-12(14)15-9(2)3/h4,9-11,13H,1,5-8H2,2-3H3/t10-,11-/m0/s1
    • InChI Key： FIZXDKZYWPGUIT-QWRGUYRKSA-N
    • SMILES： N1CC[C@@H](CC(OC(C)C)=O)[C@@H](C=C)C1

4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
1.2 Solvents: Tetrahydrofuran ;  < 20 °C
1.3 Reagents: Oxygen ;  3 h, 0 °C → rt
1.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

Production Method 2

Reaction Conditions
1.1 Reagents: Benzophenone ,  Potassium tert-butoxide Solvents: Toluene ;  16 h, reflux; reflux → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C
2.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
2.2 Solvents: Tetrahydrofuran ;  < 20 °C
2.3 Reagents: Oxygen ;  3 h, 0 °C → rt
2.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

Production Method 3

Reaction Conditions
1.1 Reagents: Dimethyl sulfoxide ,  Oxalyl chloride Solvents: Dichloromethane ;  -78 °C; 20 min, -78 °C
1.2 Solvents: Dichloromethane ;  40 min, -78 °C
1.3 Reagents: Triethylamine ;  -78 °C; -78 °C → 0 °C; 1 h, 0 °C
1.4 Reagents: Water ;  0 °C
2.1 Reagents: Potassium hydroxide Solvents: Acetonitrile ,  tert-Butanol ;  0 °C; 24 h, 0 °C
3.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  15 min, 180 °C
3.2 Reagents: Oxygen ;  24 h, rt
3.3 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
4.1 Reagents: Benzophenone ,  Potassium tert-butoxide Solvents: Toluene ;  16 h, reflux; reflux → 0 °C
4.2 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C
5.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
5.2 Solvents: Tetrahydrofuran ;  < 20 °C
5.3 Reagents: Oxygen ;  3 h, 0 °C → rt
5.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

Production Method 4

Reaction Conditions
1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  30 min, 0 °C; 30 min, 0 °C
1.2 Reagents: Sodium hydroxide Solvents: Water
2.1 Reagents: Dimethyl sulfoxide ,  Oxalyl chloride Solvents: Dichloromethane ;  -78 °C; 20 min, -78 °C
2.2 Solvents: Dichloromethane ;  40 min, -78 °C
2.3 Reagents: Triethylamine ;  -78 °C; -78 °C → 0 °C; 1 h, 0 °C
2.4 Reagents: Water ;  0 °C
3.1 Reagents: Potassium hydroxide Solvents: Acetonitrile ,  tert-Butanol ;  0 °C; 24 h, 0 °C
4.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  15 min, 180 °C
4.2 Reagents: Oxygen ;  24 h, rt
4.3 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
5.1 Reagents: Benzophenone ,  Potassium tert-butoxide Solvents: Toluene ;  16 h, reflux; reflux → 0 °C
5.2 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C
6.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
6.2 Solvents: Tetrahydrofuran ;  < 20 °C
6.3 Reagents: Oxygen ;  3 h, 0 °C → rt
6.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

Production Method 5

Reaction Conditions
1.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  15 min, 180 °C
1.2 Reagents: Oxygen ;  24 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
2.1 Reagents: Benzophenone ,  Potassium tert-butoxide Solvents: Toluene ;  16 h, reflux; reflux → 0 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C
3.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
3.2 Solvents: Tetrahydrofuran ;  < 20 °C
3.3 Reagents: Oxygen ;  3 h, 0 °C → rt
3.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

Production Method 6

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Acetonitrile ,  tert-Butanol ;  0 °C; 24 h, 0 °C
2.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  15 min, 180 °C
2.2 Reagents: Oxygen ;  24 h, rt
2.3 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
3.1 Reagents: Benzophenone ,  Potassium tert-butoxide Solvents: Toluene ;  16 h, reflux; reflux → 0 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C
4.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
4.2 Solvents: Tetrahydrofuran ;  < 20 °C
4.3 Reagents: Oxygen ;  3 h, 0 °C → rt
4.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

Production Method 7

Reaction Conditions
1.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ;  -45 °C; 20 min, -45 °C
1.2 Solvents: Dichloromethane
1.3 -45 °C; -45 °C → rt; 16 h, rt
2.1 Reagents: Potassium hydroxide Solvents: Acetonitrile ,  tert-Butanol ;  0 °C; 24 h, 0 °C
3.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  15 min, 180 °C
3.2 Reagents: Oxygen ;  24 h, rt
3.3 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
4.1 Reagents: Benzophenone ,  Potassium tert-butoxide Solvents: Toluene ;  16 h, reflux; reflux → 0 °C
4.2 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C
5.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
5.2 Solvents: Tetrahydrofuran ;  < 20 °C
5.3 Reagents: Oxygen ;  3 h, 0 °C → rt
5.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

Production Method 8

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, rt
1.3 Solvents: Tetrahydrofuran ;  rt; 20 min, rt
1.4 Reagents: Water ,  Sodium borohydride ;  10 min, rt; 4 h, rt
1.5 Reagents: Water
2.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ;  -45 °C; 20 min, -45 °C
2.2 Solvents: Dichloromethane
2.3 -45 °C; -45 °C → rt; 16 h, rt
3.1 Reagents: Potassium hydroxide Solvents: Acetonitrile ,  tert-Butanol ;  0 °C; 24 h, 0 °C
4.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  15 min, 180 °C
4.2 Reagents: Oxygen ;  24 h, rt
4.3 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt
5.1 Reagents: Benzophenone ,  Potassium tert-butoxide Solvents: Toluene ;  16 h, reflux; reflux → 0 °C
5.2 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C
6.1 Reagents: Potassium tert-butoxide ,  Oxygen Solvents: Isopropanol ,  Tetrahydrofuran ;  1 h, 0 °C
6.2 Solvents: Tetrahydrofuran ;  < 20 °C
6.3 Reagents: Oxygen ;  3 h, 0 °C → rt
6.4 Reagents: Sulfuric acid Solvents: Water ;  0 °C
Reference
Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
Illa, Ona; et al, Journal of the American Chemical Society, 2010, 132(6), 1828-1830

4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)- Raw materials

4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)- Preparation Products

4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)- Related Literature

345223-64-5 (4-Piperidineacetic acid, 3-ethenyl-, 1-methylethyl ester, (3R,4S)-) Related Products

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