Hydrochloric Acid → HCID 67050764, compound

HRID 1629447Notes

Reaction equation

HRID 1629447 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][CH3:14])[C@H:9]1[C:15](=[O:17])[NH2:16])=O)(C)(C)C.CO.[ClH:20]>>[ClH:20].[CH3:14][O:13][C@H:10]1[CH2:11][CH2:12][NH:8][C@@H:9]1[C:15]([NH2:16])=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58204623HCID 58204623, compound

Product 1

HCID 67050764HCID 67050764, compoundYield 38%

Procedure

(2S,3S)-2-Carbamoyl-3-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester (120 mg, 0.49 mmol) was stirred in hydrochloric acid (5 mL, 3M in methanol) and methanol for 4 h. The reaction mixture was concentrated in vacuo and the residue triturated in diethyl ether and methanol to give (2S,3S)-3-Methoxy-pyrrolidine-2-carboxylic acid amide hydrochloride salt as a white solid (69 mg, 38%). 1H NMR 400 MHz (DMSO-d6) δ: 8.28 (1 H, br, s), 7.82 (1 H, br, s), 4.23 (1 H, m), 4.11-4.10 (1 H, m), 3.37 (1 H, m), 3.35 (3 H, s), 3.19-3.16 (1 H, m), 2.07 (1 H, m), 1.84-1.83 (1 H, m)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue triturated in diethyl ether

Sources & evidence

ORD record
ord-e36bb1e510a2499aa8b0172bc3ca4de8
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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