trans-4-Azido-n-tert-butoxycarbonyl-d-proline methyl ester → 1-tert-Butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate

HRID 2185417Notes

Reaction equation

HRID 2185417 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C@H:4]1[CH2:8][C@H:7]([N:9]=[N+]=[N-])[CH2:6][N:5]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>[Pd].CO>[CH3:1][O:2][C:3](=[O:19])[C@H:4]1[CH2:8][C@H:7]([NH2:9])[CH2:6][N:5]1[C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13]

Participants

4

Reactant 1

HCID 58928014trans-4-Azido-n-tert-butoxycarbonyl-d-proline methyl ester

Product 1

HCID 15194991-tert-Butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylateYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-4-azido-N-tert-butoxycarbonyl-D-proline methyl ester (C, 1.04 g) and 10% palladium on activated carbon (500 mg) in methanol (30 mL) was stirred at room temperature for 1.5 hr under hydrogen. The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo to give the title compound (0.90 g) as a colorless oil.

Workup

  1. customThe catalysts were removed by filtration
  2. washwashed with methanol
  3. customThe combined organic layers were evaporated in vacuo

Sources & evidence

ORD record
ord-5a16262d36664a818f7fe7761ef7a404
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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