Ammonia → (S)-2-Methylpyrrolidine-2-carboxamide

HRID 1430113Notes

Reaction equation

HRID 1430113 reaction equation
C([O:5][C:6]([C@:8]1([CH3:13])[CH2:12][CH2:11][CH2:10][NH:9]1)=O)CCC.[NH3:14]>CO>[CH3:13][C@@:8]1([C:6]([NH2:14])=[O:5])[CH2:12][CH2:11][CH2:10][NH:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58092703HCID 58092703, compound

Product 1

HCID 14829625(S)-2-Methylpyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-2-methyl-pyrrolidine-2-carboxylic acid butyl ester (2.3 g) in a 7 M solution of ammonia in methanol (22.2 ml) is heated in a bomb at 70° C. for 10 days. Evaporation of the reaction mixture and trituration with hexanes (20 ml) gives the title compound as an off-white solid. 1H nmr (d6-DMSO, 400 MHz) 7.40 (s, 1H), 6.89 (s, 1H), 2.95-2.84 (m, 1H), 2.72-2.60 (m, 1H), 2.06-1.95 (m, 1H), 1.66-1.44 (m, 2H), 1.42-1.30 (m, 1H), 1.22 (s, 3H).

Workup

  1. customEvaporation of the reaction mixture and trituration with hexanes (20 ml)

Sources & evidence

ORD record
ord-fcedc9b7d937496eae9bd0750cfa2f47
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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