1,1-Dimethylethyl N-[3-methyl-1-(phenylmethyl)-3-pyrrolidinyl]carbamate → tert-butyl N-(3-methylpyrrolidin-3-yl)carbamate

HRID 72118Notes

Reaction equation

HRID 72118 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:13])[CH2:9]1)C1C=CC=CC=1>CCO.[Pd]>[CH3:13][C:10]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 104937341,1-Dimethylethyl N-[3-methyl-1-(phenylmethyl)-3-pyrrolidinyl]carbamate

Product 1

HCID 10798104tert-butyl N-(3-methylpyrrolidin-3-yl)carbamateYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 1-benzyl-3-methylpyrrolidin-3-ylcarbamate (1.17 g, 4.0 mmol) in EtOH (40 mL) was added to 10% Pd on C and shaken under 45 psi of H2 for 3 h. The mixture was filtered through Celite and concentrated to afford tert-butyl 3-methylpyrrolidin-3-ylcarbamate (0.59 g, 73%). LC-MS Method 1 tR=0.72 min, m/z=201.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a10bbe61686241568c560e6b32da5f07
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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