Ammonium formate → HCID 59312404, compound

HRID 910449Notes

Reaction equation

HRID 910449 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6](=[O:27])[N:7]([CH3:8])[CH:9]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][NH:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59312433HCID 59312433, compound

Product 1

HCID 59312404HCID 59312404, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of ((3RS,4SR)-1-Benzyl-4-phenyl-pyrrolidin-3-yl)-methyl-carbamic acid tert-butyl ester (2.03 g, 5.56 mmol) in MeOH (20 ml) at RT, was added ammonium formate (1.60 g, 25.4 mmol) and palladium on charcoal (0.40 g, 10%) The reaction mixture was stirred for 2 hours, filtrate on celite and concentrated under vacuo. The residue was purified by column chromatography (CH2Cl2/MeOH, 9/1) to give 0.57 g (41%) of the title product as a waxy solid.

Workup

  1. concentrationfiltrate on celite and concentrated under vacuo
  2. customThe residue was purified by column chromatography (CH2Cl2/MeOH, 9/1)

Sources & evidence

ORD record
ord-8a803baf07004cd9b2f8a3590197daaf
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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