3-Amino-1-benzylpyrrolidine-3-carboxylic acid → 3-Aminopyrrolidine-3-carboxylic acid

HRID 861208Notes

Reaction equation

HRID 861208 reaction equation
[NH2:1][C:2]1([C:14]([OH:16])=[O:15])[CH2:6][CH2:5][N:4](CC2C=CC=CC=2)[CH2:3]1.[H][H]>>[NH2:1][C:2]1([C:14]([OH:16])=[O:15])[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

3

Reactant 2

HCID 108570113-Amino-1-benzylpyrrolidine-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 4157633-Aminopyrrolidine-3-carboxylic acid

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-8a7845f44951431d8a783570fecc7df4
Source dataset
uspto-grants-1998_02
Patent number
US05714164

Reaction notes

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