Production Method 1

15252-44-5

872-32-2

Reaction Conditions

1.1 Catalysts: Samarium, [bis[P,P-diphenyl-N-(trimethylsilyl)phosphinimyl-κN]methyl-κC](η8-1,3,… Solvents: Benzene-d6 ;  120 °C

Reference

Cyclooctatetraene Complexes of Yttrium and the Lanthanides with Bis(phosphinimino)methanides: Synthesis, Structure, and Hydroamination/Cyclization Catalysis

Panda, Tarun K.; et al, Organometallics, 2005, 24(9), 2197-2202

Production Method 2

84702-73-8

872-32-2

Reaction Conditions

1.1 Catalysts: Triphenylphosphine Solvents: Diethyl ether

Reference

Triphenylphosphine

Cobb, Jeff E.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 3

14468-90-7

917-54-4

872-32-2

Reaction Conditions

1.1 Solvents: Diethyl ether

Reference

Selective nucleophilic addition reactions of alkyllithium reagents with N-(trimethylsilyl)lactams. Synthesis of cyclic ketimines

Hua, Duy H.; et al, Journal of Organic Chemistry, 1990, 55(11), 3682-4

Production Method 4

70912-52-6

872-32-2

Reaction Conditions

Reference

Cyclic β-enamino ester decarboxylation with boric acid: a convenient synthesis of cyclic imines

Bacos, Daniel; et al, Tetrahedron Letters, 1987, 28(21), 2353-4

Production Method 5

5891-21-4

872-32-2

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Diethyl ether

Reference

Syntheses of novel carbo- and heteropolycycles. V. Reactivity in some intramolecular aza-Wittig reactions

Eguchi, Shoji; et al, Nippon Kagaku Kaishi, 1987, (7), 1250-4

Production Method 6

917-54-4

5332-06-9

872-32-2

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Benzene

Reference

Cyclization of ω-halonitriles with organolithiums

Gallulo, Vincent; et al, Organic Preparations and Procedures International, 1989, 21(3), 297-301

Production Method 7

87267-07-0

872-32-2

Reaction Conditions

1.1 Reagents: Hydrochloric acid

Reference

Synthesis and thermolysis of O-alkyl-N-vinylhydroxylamine derivatives

Shatzmiller, Shimon; et al, Liebigs Annalen der Chemie, 1983, (6), 897-905

Production Method 8

5332-06-9

872-32-2

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Benzene

Reference

Synthesis of cyclic imines by addition of Grignard reagents to ω-bromonitriles

Fry, Douglas F.; et al, Synlett, 1994, (10), 836-8

Production Method 9

917-54-4

5264-35-7

872-32-2

Reaction Conditions

Reference

Reaction of organolithium reagents with lactim ethers: preparation of cyclic 2-alkyl imines or 2,2-dialkyl amines

Zezza, Charles A.; et al, Journal of Organic Chemistry, 1984, 49(23), 4397-9

Production Method 10

848652-44-8

872-32-2

Reaction Conditions

Reference

Product class 7: imines

Tehrani, K. Abbaspour; et al, Science of Synthesis, 2004, 27, 245-312

Production Method 11

91640-80-1

872-32-2

Reaction Conditions

1.1 Catalysts: Iridium(1+), dicarbonyl[2,2′-methylenebis[1-methyl-1H-imidazole-κN3]]-, (SP-4-2)… Solvents: THF-d8 ;  12 h, 60 °C

Reference

Late Transition Metal Catalyzed Intramolecular Hydroamination: The Effect of Ligand and Substrate Structure

Burling, Suzanne; et al, Organometallics, 2007, 26(17), 4335-4343

Production Method 12

15252-44-5

872-32-2

Reaction Conditions

1.1 Catalysts: Samarium, [bis[P,P-diphenyl-N-(trimethylsilyl)phosphinimyl-κN]methyl-κC](η8-1,3,… Solvents: Benzene-d6 ;  120 °C

Reference

A samarium cyclooctatetraene complex as catalyst for hydroamination/cyclisation catalysis

Zulys, Agustino; et al, Chemical Communications (Cambridge, 2004, (22), 2584-2585

Production Method 13

15252-44-5

872-32-2

Reaction Conditions

1.1 Catalysts: Potassium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ,  1808207-42-2 Solvents: Benzene-d6 ;  1 h, rt

Reference

Diverse reactivity of a tricoordinate organoboron L2PhB: (L = oxazol-2-ylidene) towards alkali metal, group 9 metal, and coinage metal precursors

Kong, Lingbing; et al, Chemical Science, 2015, 6(5), 2893-2902

Production Method 14

84702-73-8

872-32-2

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Pentane

Reference

Reaction of ω-azido ketones with triphenylphosphine. A general synthesis of cyclic imines

Vaultier, M.; et al, Bulletin de la Societe Chimique de France, 1986, (1), 83-92

Production Method 15

84702-73-8

872-32-2

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Diethyl ether

Reference

The use of ω-iodo azides as primary protected electrophilic reagents. Alkylation of some carbanions derived from active methylene compounds and N,N-dimethylhydrazones

Khoukhi, Mostafa; et al, Tetrahedron Letters, 1986, 27(9), 1031-4

Production Method 16

5891-21-4

872-32-2

Reaction Conditions

1.1 Reagents: Hydrazine Catalysts: Potassium phthalimide

Reference

Preparation of 2-methyl-1-pyrroline as a photochemical dye intermediate

, Poland, , ,

Production Method 17

872-32-2

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water
1.2 Reagents: Sodium bicarbonate Solvents: Dichloromethane

Reference

Reactions of N-phosphorylated aziridines with dianions derived from ethyl acetoacetate and 1,3-diketones: new route to substituted pyrrolines and pyrrolidines

Osowska-Pacewicka, Krystyna; et al, Synthetic Communications, 1998, 28(7), 1127-1137

Production Method 18

31536-38-6

872-32-2

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water
1.2 Reagents: Potassium hydroxide

Reference

Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines

Nenajdenko, Valentine G.; et al, Tetrahedron, 2004, 60(51), 11719-11724

Production Method 19

5264-35-7

872-32-2

Reaction Conditions

1.1 Reagents: Ammonium chloride Solvents: Tetrahydrofuran

Reference

Certain 1-pyrroline derivatives

Etienne, Andre; et al, Compt. Rend., 1964, 259(16), 2660-3

Production Method 20

917-54-4

628-20-6

872-32-2

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Benzene

Reference

Cyclization of ω-halonitriles with organolithiums

Gallulo, Vincent; et al, Organic Preparations and Procedures International, 1989, 21(3), 297-301

Production Method 21

872-32-2

Reaction Conditions

1.1 -
1.2 Reagents: Magnesium oxide

Reference

A convenient synthesis of myosmine

Ravi, S.; et al, Oriental Journal of Chemistry, 2000, 16(3), 521-523

Production Method 22

872-32-2

Reaction Conditions

1.1 -
2.1 Catalysts: Calcium oxide

Reference

A convenient synthesis of 2-methyl/ethyl-Δ1-pyrrolines

Ananthapadmanabhan, S.; et al, Indian Journal of Chemistry, 1988, (6),

Production Method 23

932-17-2

872-32-2

Reaction Conditions

1.1 Catalysts: Calcium oxide

Reference

A convenient synthesis of 2-methyl/ethyl-Δ1-pyrrolines

Ananthapadmanabhan, S.; et al, Indian Journal of Chemistry, 1988, (6),

2-Methyl-1-pyrroline Raw materials

• N-Trimethylsilyl-2-pyrrolidone
• 2,2-dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione
• 1-Acetyl-2-pyrrolidone
• pent-4-yn-1-amine
• 2-Pyrrolidinone,3-acetyl-
• 5-chloropentan-2-one
• Methyllithium (1.6M in Diethyl Ether)
• 2-Methoxy-1-pyrroline
• pent-3-yn-1-amine
• 2-PENTANONE, 5-AZIDO-
• 4-chlorobutanenitrile
• 4-Bromobutyronitrile
• 2-PENTANONE, 5-[(TRIPHENYLPHOSPHORANYLIDENE)AMINO]-
• 1-Ethoxy-2-methylenepyrrolidine

2-Methyl-1-pyrroline Preparation Products

• 2-Methyl-1-pyrroline (872-32-2)

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• 3338-04-3(2H-Azepine,7-ethyl-3,4,5,6-tetrahydro-)
• 1462-94-8(Pyridine,2-butyl-3,4,5,6-tetrahydro-)
• 1192-29-6(5-Ethyl-3,4-dihydro-2H-pyrrole)
• 88226-75-9(1-Butanamine, N-(1-ethylbutylidene)-, (E)-)
• 929269-44-3(5-methyl-3,4-dihydro-2H-pyrrole hydrochloride)
• 20764-18-5(1-Butanamine, N-(1-methylbutylidene)-)
• 5960-99-6(2H-Azepine-7-pentanamine,3,4,5,6-tetrahydro-)
• 10599-80-1(1-Butanamine,N-(1-propylbutylidene)-)
• 64319-86-4(2H-Pyrrole, 5-butyl-3,4-dihydro-)
• 88226-73-7(1-Butanamine, N-(1-ethylbutylidene)-, (Z)-)