(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate → (2S,4S)-1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

HRID 425127Notes

Reaction equation

HRID 425127 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:10]=[N+]=[N-])[CH2:7][N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH2:10])[CH2:7][N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4]

Participants

4

Reactant 1

HCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Product 1

HCID 5200425(2S,4S)-1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylateYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2S,4S)-4-azidopyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (8.5 g, 31 mmol) and Pd/C (10% w/w, 2.0 g) were stirred in MeOH (150 mL) at room temperature under an atmosphere of hydrogen for 48 hours. The mixture was filtered and the filtrate evaporated to afford the title compound (7.34 g, 30 mmol), which was used without further purification. MS m/z: [M+H]+ calcd for C11H20N2O4, 244.3. found 245.3.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-8401b4df7de1488491efa1369d20c2a4
Source dataset
uspto-grants-2012_01
Patent number
US08106082B2

Reaction notes

Loading…