HCID 89533690, compound → HCID 89533688, compound

HRID 1050974Notes

Reaction equation

HRID 1050974 reaction equation
[F:1][C:2]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5]>CO.[Pd]>[NH2:19][C:18]1[C:2]([F:1])=[C:3]([CH:15]=[CH:16][CH:17]=1)[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5]

Participants

4

Reactant 1

HCID 89533690HCID 89533690, compound

Product 1

HCID 89533688HCID 89533688, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 25.0 g (0.08 mol, 1.0 eq) of methyl (S)-1-(2-fluoro-3-nitrobenzoyl)pyrrolidine-2-carboxylate in 250 ml of methanol in the presence of 7.0 g (28% by weight) of palladium on carbon at 10% was stirred under a hydrogen atmosphere at ambient temperature for 4 days. The reaction medium was filtered through celite and washed with 100 ml of methanol. The filtrate was evaporated. 22.80 g of methyl (S)-1-(3-amino-2-fluorobenzoyl)pyrrolidine-2-carboxylate were obtained in the form of a light oil. Quantitative yield.

Workup

  1. filtrationThe reaction medium was filtered through celite
  2. washwashed with 100 ml of methanol
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a8c4ff1935594116afe4414361de9fd6
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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