Cas no 86953-81-3 (tert-butyl 2-hydroxypiperidine-1-carboxylate)

tert-butyl 2-hydroxypiperidine-1-carboxylate structure
86953-81-3 structure
Product Name:tert-butyl 2-hydroxypiperidine-1-carboxylate
CAS No:86953-81-3
MF:C10H19NO3
MW:201.262763261795
MDL:MFCD09031186
CID:708656
PubChem ID:10655694
Update Time:2024-10-26

tert-butyl 2-hydroxypiperidine-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1-Piperidinecarboxylicacid, 2-hydroxy-, 1,1-dimethylethyl ester
    • tert-butyl 2-hydroxypiperidine-1-carboxylate
    • 1-t-butoxycarbonyl-2-hydroxypiperidine
    • 2-hydroxy-1-(tert-butoxycarbonyl)piperidine
    • 2-hydroxy-N-Boc-piperidine
    • N-(tert-butoxycarbonyl)-2-hydroxypiperidine
    • N-boc-2-hydroxypiperidine
    • N-Boc-piperidinol
    • N-tert-butoxycarbonyl-2-piperidinol
    • 1,1-Dimethylethyl 2-hydroxy-1-piperidinecarboxylate (ACI)
    • ZBCXTNPVDVWHNC-UHFFFAOYSA-N
    • 86953-81-3
    • AS-52737
    • AKOS015962867
    • 1-Boc-2-Hydroxypiperidine
    • SY276983
    • hydroxy-1-tert-butoxycarbonylpiperidine
    • MB06824
    • MFCD09031186
    • SCHEMBL1427524
    • CS-0048414
    • P15565
    • DTXSID90443048
    • MDL： MFCD09031186
    • Inchi： 1S/C10H19NO3/c1-10(2,3)14-9(13)11-7-5-4-6-8(11)12/h8,12H,4-7H2,1-3H3
    • InChI Key： ZBCXTNPVDVWHNC-UHFFFAOYSA-N
    • SMILES： O=C(N1C(O)CCCC1)OC(C)(C)C

Computed Properties

  • Exact Mass: 201.13600
  • Monoisotopic Mass: 201.13649347g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 210
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2
  • Topological Polar Surface Area: 49.8?2

Experimental Properties

  • PSA: 49.77000
  • LogP: 1.66370

tert-butyl 2-hydroxypiperidine-1-carboxylate Customs Data

  • HS CODE：2933399090
  • Customs Data：

    China Customs Code:

    2933399090

    Overview:

    2933399090. Other compounds with non fused pyridine rings in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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tert-butyl 2-hydroxypiperidine-1-carboxylate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  30 min, 0 °C
1.2 0 °C; 2 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt
1.4 Reagents: Vitride Solvents: Dichloromethane ,  Toluene ;  2 h, -78 °C
1.5 Reagents: Methanol ;  -78 °C
1.6 Reagents: Potassium sodium tartrate Solvents: Water ;  > 1 h, rt
Reference
Bronsted Acid-Catalyzed Aza-Ferrier Reaction of N,O-Allenyl Acetals: Synthesis of β-Amino-α-methylene Aldehydes
Tayama, Eiji ; et al, Journal of Organic Chemistry, 2020, 85(14), 9405-9414

Production Method 2

Reaction Conditions
1.1 Reagents: Diisobutylaluminum hydride Solvents: Toluene
Reference
A Facile Preparation of Enecarbamates
Dieter, R. Karl; et al, Journal of Organic Chemistry, 1996, 61(12), 4180-4184

Production Method 3

Reaction Conditions
1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  -78 °C
Reference
Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines
Gawley, Robert E.; et al, Tetrahedron Letters, 2004, 45(8), 1759-1761

Production Method 4

Reaction Conditions
1.1 Reagents: Zirconocene chloride hydride Solvents: Tetrahydrofuran ;  rt
Reference
Hydrozirconation of four-, five-, six- and seven-membered N-alkoxycarbonyl lactams to lactamols
Piperno, Anna; et al, Tetrahedron Letters, 2011, 52(51), 6880-6882

Production Method 5

Reaction Conditions
1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 2 h, -78 °C
1.2 Reagents: Potassium sodium tartrate Solvents: Water ;  -78 °C
Reference
Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives
Chen, Cheng; et al, Organic & Biomolecular Chemistry, 2017, 15(25), 5364-5372

Production Method 6

Reaction Conditions
1.1 Reagents: Dimethyl sulfoxide ,  Oxalyl chloride Solvents: Dichloromethane ;  -78 °C; 5 min, -78 °C
1.2 Solvents: Dichloromethane ;  -78 °C; 25 min, -78 °C
1.3 Reagents: Diisopropylethylamine ;  -78 °C → -30 °C; 30 min, -30 °C
Reference
A carbodiimide-mediated P-C bond-forming reaction: Mild amidoalkylation of P-nucleophiles by Boc-aminals
Kokkala, Paraskevi; et al, Organic Letters, 2021, 23(5), 1726-1730

Production Method 7

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  1 h, 0 °C
1.2 2 h, 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water
1.4 Reagents: Vitride Solvents: Dichloromethane ,  Toluene ;  2 h, -78 °C
1.5 Reagents: Methanol ,  Potassium sodium tartrate Solvents: Water ;  -78 °C; -78 °C → rt; 1 h, rt
Reference
1,4-Elimination/Bronsted acid catalyzed aza-Ferrier reaction sequence as an entry to β-amino-β,γ-unsaturated aldehydes
Tayama, Eiji; et al, Tetrahedron, 2013, 69(13), 2745-2752

Production Method 8

Reaction Conditions
1.1 Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  12 h, rt
1.2 Reagents: Ammonium chloride
2.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  rt; 2 h, -78 °C
2.2 Reagents: Potassium sodium tartrate Solvents: Ethyl acetate
Reference
In(OTf)3-catalyzed N-α phosphonylation of N,O-acetals with triethyl phosphite
Sun, Jian-Ting; et al, Organic & Biomolecular Chemistry, 2022, 20(33), 6571-6581

Production Method 9

Reaction Conditions
1.1 Reagents: Lithium triethylborohydride Solvents: Tetrahydrofuran ;  30 min, -78 °C; -78 °C → 0 °C
1.2 Reagents: Sodium bicarbonate ,  Hydrogen peroxide Solvents: Water ;  30 min, 0 °C
Reference
One-Pot Formation of Piperidine- and Pyrrolidine-Substituted Pyridinium Salts via Addition of 5-Alkylaminopenta-2,4-dienals to N-Acyliminium Ions: Application to the Synthesis of (±)-Nicotine and Analogs
Peixoto, Sabrina; et al, Organic Letters, 2010, 12(21), 4760-4763

Production Method 10

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Tempo ,  Laccase Solvents: tert-Butyl methyl ether ,  Water ;  18 h, 30 °C
Reference
Laccase/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO): An efficient catalytic system for selective oxidations of primary hydroxy and amino groups in aqueous and biphasic media
Diaz-Rodriguez, Alba; et al, Advanced Synthesis & Catalysis, 2014, 356(10), 2321-2329

Production Method 11

Reaction Conditions
1.1 Solvents: Dichloromethane ;  24 h, rt
2.1 Reagents: Oxygen Catalysts: Tempo ,  Laccase Solvents: tert-Butyl methyl ether ,  Water ;  18 h, 30 °C
Reference
Laccase/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO): An efficient catalytic system for selective oxidations of primary hydroxy and amino groups in aqueous and biphasic media
Diaz-Rodriguez, Alba; et al, Advanced Synthesis & Catalysis, 2014, 356(10), 2321-2329

Production Method 12

Reaction Conditions
1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 2 h, -78 °C
1.2 Reagents: Potassium sodium tartrate Solvents: Water ;  3 h, rt
Reference
Backbone-Modified C2-Symmetrical Chiral Bisphosphine TMS-QuinoxP*: Asymmetric Borylation of Racemic Allyl Electrophiles
Iwamoto, Hiroaki ; et al, Journal of the American Chemical Society, 2021, 143(17), 6413-6422

Production Method 13

Reaction Conditions
1.1 Catalysts: D-Proline Solvents: Dimethyl sulfoxide ;  20 min, rt
Reference
Total Synthesis of (±)- and (-)-Actinophyllic Acid
Martin, Connor L.; et al, Journal of the American Chemical Society, 2010, 132(13), 4894-4906

Production Method 14

Reaction Conditions
1.1 Catalysts: 4-(Dimethylamino)pyridine Solvents: Acetonitrile ;  3 h, 20 °C
2.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 2 h, -78 °C
2.2 Reagents: Potassium sodium tartrate Solvents: Water ;  -78 °C
Reference
Synthesis of functionalised azepanes and piperidines from bicyclic halogenated aminocyclopropane derivatives
Chen, Cheng; et al, Organic & Biomolecular Chemistry, 2017, 15(25), 5364-5372

tert-butyl 2-hydroxypiperidine-1-carboxylate Raw materials

tert-butyl 2-hydroxypiperidine-1-carboxylate Preparation Products

tert-butyl 2-hydroxypiperidine-1-carboxylate Related Literature

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