Ammonia → hexahydro-1H-pyrrolizine-7a-carbonitrile

Reaction equation

CC(C)(O)[C:3]#[N:4].[NH3:7].Cl[CH2:9][CH2:10][CH2:11][C:12](=O)[CH2:13][CH2:14][CH2:15]Cl.[OH-].[Na+]>>[C:3]([C:12]12[CH2:13][CH2:14][CH2:15][N:7]1[CH2:9][CH2:10][CH2:11]2)#[N:4]

Participants

Reactant 4

HCID 222Ammonia

HCID 6406Acetone Cyanohydrin

HCID 14798Sodium Hydroxide

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

Product 1

HCID 11029899hexahydro-1H-pyrrolizine-7a-carbonitrileYield 89%

Conditions

Temperature: 20 °C

Procedure

To a solution of aceton cyanohydrin (2.3 g, 27 mmol) saturated with ammonia, 1,7-dichloro-4-heptanone (0.50 g, 2.7 mmol) was added dropwise at 20° C. The resulting solution was stirred for 48 hours at 20° C. under ammonia gas atmosphere. To the reaction mixture, 0.1N-NaOH was added to extract with methylene chloride. The extract was dried over anhydrous sodium sulfate, concentrated and distilled in vacuo to afford 0.33 g of the desired compound (Yield: 89%).