Potassium Cyanide → 3-Amino-1-benzylpyrrolidine-3-carbonitrile

HRID 2255849Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+:15].[C-:16]#[N:17].[K+]>>[NH2:15][C:10]1([C:16]#[N:17])[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1

Participants

Reactant 3

HCID 9032Potassium Cyanide

HCID 25517Ammonium Chloride

HCID 698901-Benzyl-3-pyrrolidinone

Product 1

HCID 220633693-Amino-1-benzylpyrrolidine-3-carbonitrile

Procedure

According to a particular variant of embodiment of this synthesis process, 1-benzyl-3-pyrrolidinone is treated with an ammoniacal solution of ammonium chloride and of potassium cyanide to obtain (±)-3-amino-1-benzyl-3-cyanopyrrolidine. This compound is then converted by acid or basic hydrolysis to (±)-3-amino-1-benzyl-3-pyrrolidinecarboxylic acid, and lastly a reduction with hydrogen, preferably a catalytic hydrogenolysis, is carried out to obtain (±)-3-amino-3-pyrrolidinecarboxylic acid or (±)-cucurbitine.

Sources & evidence

ORD record: ord-f03766eee2514b9cbdaed4616e669b88
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05653997

Reaction notes

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