(S)-benzyl 3-(tert-butoxycarbonylamino)-3-methylpyrrolidine-1-carboxylate → (S)-tert-Butyl (3-methylpyrrolidin-3-yl)carbamate

HRID 338829Notes

Reaction equation

HRID 338829 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].[H][H]>C(O)C.[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

5

Reactant 2

HCID 51041670(S)-benzyl 3-(tert-butoxycarbonylamino)-3-methylpyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 51041669(S)-tert-Butyl (3-methylpyrrolidin-3-yl)carbamateYield 97.45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-benzyl 3-(tert-butoxycarbonylamino)-3-methylpyrrolidine-1-carboxylate (29.35 g, 87.77 mmol) and 10% Pd/C (4.670 g, 4.388 mmol) in ethanol (50 mL) was charged with hydrogen (1 atmosphere) and stirred at ambient temperature overnight. The catalyst was removed by filtration and washed with ethanol (2×50 mL). The filtrated was concentrated under reduced pressure to give (S)-tert-butyl 3-methylpyrrolidin-3-ylcarbamate (17.13 g, 85.53 mmol, 97.45% yield) as an oil. MS APCI (+) m/z 201 (M+1) detected.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol (2×50 mL)
  3. concentrationThe filtrated was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5d1079d93c8b49c29fc8b3ce71ae7e83
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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