Benzyl 3-[(tert-butoxycarbonyl)amino]-3-methylpyrrolidine-1-carboxylate → tert-butyl N-(3-methylpyrrolidin-3-yl)carbamate

HRID 1923657Notes

Reaction equation

HRID 1923657 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([CH3:24])[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[CH3:24][C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH2:12][NH:11][CH2:10]1

Participants

4

Reactant 1

HCID 60205236Benzyl 3-[(tert-butoxycarbonyl)amino]-3-methylpyrrolidine-1-carboxylate

Product 1

HCID 10798104tert-butyl N-(3-methylpyrrolidin-3-yl)carbamateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 3-(tert-butoxycarbonylamino)-3-methylpyrrolidine-1-carboxylate (2.00 g, 5.98 mmol) and 10% Pd/C (0.32 g, 0.30 mmol) in MeOH (20 mL) were stirred under 1 atmosphere of H2 for 1 hour. The catalyst was removed by filtration and washed with methanol. The filtrate was concentrated to give tert-butyl 3-methylpyrrolidin-3-ylcarbamate (1.15 g, 96%) as a solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-166938a5400f40619f575bbba8096d38
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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