Ammonia → (2S,4R)-4-hydroxypyrrolidine-2-carboxamide

HRID 1430108Notes

Reaction equation

HRID 1430108 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][NH:12]1)=O)C1C=CC=CC=1.[NH3:17]>>[OH:16][C@H:14]1[CH2:13][NH:12][C@H:11]([C:9]([NH2:17])=[O:8])[CH2:15]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 6993393benzyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylate

Product 1

HCID 2452255(2S,4R)-4-hydroxypyrrolidine-2-carboxamide

Procedure

A solution of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid benzyl ester (1 g) in 880 ammonia (5 ml) is stirred for 18 hours then evaporated and triturated with diethyl ether to give the title compound as a white solid. 1H nmr (d6-DMSO, 400 MHz) 9.15 (s, br, 1H), 8.04 (s, 1H), 7.63 (s, 1H), 5.56 (s, 1H), 4.40 (s, 1H), 4.27-4.16 (m, 1H), 3.27 (d, J=7 Hz, 1H), 3.02 (d, J=7 Hz, 1H), 2.33-2.19 (m, 1H), 1.89-1.76 (m, 1H).

Workup

  1. customthen evaporated
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-efa4a5d7f5d74e96b7aaeaa886fa74a1
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

Loading…