2-Amino-2-methylpropionitrile → hexahydro-1H-pyrrolizine-7a-carbonitrile

Reaction equation

[NH2:1][C:2](C)(C)C#N.Cl[CH2:8][CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][CH2:14]Cl.[NH3:17].CO>>[C:2]([C:11]12[CH2:12][CH2:13][CH2:14][N:17]1[CH2:8][CH2:9][CH2:10]2)#[N:1]

Participants

Reactant 3

HCID 880222-Amino-2-methylpropionitrile

HCID 2467491,7-Dichloro-heptan-4-one

HCID 21705897Ammonia methanol

Product 1

HCID 11029899hexahydro-1H-pyrrolizine-7a-carbonitrileYield 82%

Procedure

A mixed solution of 2-amino-2-methylpropanenitrile (41.4 g, 492 mmol) and 1,7-dichloro-4-heptanone (30.0 g, 164 mmol) in 220 ml of 16% NH3 /MeOH solution was stirred for 24 hours at 20° C. The resulting reaction mixture was concentrated in vacuo to remove MeOH therefrom, added 0.1N NaOH to the residue, which was extracted with methylene chloride, and the extract was dried over anhydrous sodium sulfate, concentrated, and distilled in vacuo to afford 18.1 g of the desired compound (Yield: 82%).