(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester → 1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

HRID 2185409Notes

Reaction equation

HRID 2185409 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 11369242(2S,4R)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester

Product 1

HCID 70099181-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylateYield 102.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trans-4-azido-N-tert-butoxycarbonyl-L-proline methyl ester (L, 2.00 g) and 10% palladium on activated carbon (601 mg) in methanol (60 mL) was stirred at room temperature for 2.5 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 (1.85 g) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.41-1.46 (m, 9H), 1.99-2.22 (m, 2H), 2.63 (br s, 2H), 3.13-3.35 (m, 1H), 3.67-3.79 (m, 2H), 3.73 (s, 3H), and 4.36-4.47 (m, 1H).

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-43d7f404f43e4c0cb61e3f7d7a0cc117
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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