(2S,4S)-tert-butyl 4-azido-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate → tert-butyl (2S,4S)-4-amino-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

HRID 1361334Notes

Reaction equation

HRID 1361334 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+]=[N-])[CH2:10][C@H:9]1[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>O1CCOCC1.[Pd]>[C:1]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 86636654(2S,4S)-tert-butyl 4-azido-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 66971238tert-butyl (2S,4S)-4-amino-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylateYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2S,4S)-1-Boc-4-azido[(dimethylamino)carbonyl]pyrrolidine (9 g, 32 mmol) prepared in Step B in dioxane (30 mL) was added dropwise Pd/C (900 mg). The reaction mixture was stirred under hydrogen condition for 24 h, filtered through Celite, and concentrated in vacuo to give the title compound as an oil (8.1 g, 98.5%).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa6fae0578324fd1af63b53dc61de431
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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