Ammonia → HCID 58204623, compound

HRID 1498475Notes

Reaction equation

HRID 1498475 reaction equation
C[O:2][C:3]([C@@H:5]1[C@@H:9]([O:10][CH3:11])[CH2:8][CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=O.[NH3:19]>CO>[C:15]([O:14][C:12]([N:6]1[CH2:7][CH2:8][C@H:9]([O:10][CH3:11])[C@H:5]1[C:3](=[O:2])[NH2:19])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66619989HCID 66619989, compound

Product 1

HCID 58204623HCID 58204623, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,3S)-3-Methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (518 mg, 2.0 mmol) was stirred in 7M ammonia in methanol (5 mL) for 4 days. The reaction mixture was concentrated in vacuo and the residue was subjected to flash chromatography (SiO2, gradient 0 to 6% methanol in DCM) to give (2S,3S)-2-Carbamoyl-3-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester (153 mg, 31%). 1H NMR 400 MHz (DMSO-d6) δ: 7.54 (1 H, br, s), 7.09 (1 H, br, s), 4.09-4.00 (1 H, m), 3.78 (1 H, m), 3.47 (1 H, m), 3.26 (3 H, s), 1.93 (3H, m), 1.37 (9 H, s)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-22ca01f7b07244d4bba6b8d6604e8379
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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