HCID 58254864, compound → tert-butyl N-(3-phenylpyrrolidin-3-yl)carbamate

HRID 10364Notes

Reaction equation

HRID 10364 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][CH2:11][N:10](CC2C=CC=CC=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 58254864HCID 58254864, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21041211tert-butyl N-(3-phenylpyrrolidin-3-yl)carbamateYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1-Benzyl-3-phenylpyrrolidin-3-yl)carbamic acid tert-butyl ester (Hagen S. E., Domagala J. M., Heifetz C. L., Sanchez J. P., Solomon M., J. Med. Chem., 1990; 33(2):849–854) (2.79 g, 7.9 mmol) in 100 mL of methanol is treated with 1.0 g of 20% Pd/C and shaken for 17 hours under 50 psi of hydrogen. The solution is filtered and concentrated to afford 2.07 g of the title compound as a foam; MS EI+: m/z 263 (MH+).

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-07031ad2da014fb091396545797a8366
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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