Ammonium formate → HCID 70154819, compound

HRID 842215Notes

Reaction equation

HRID 842215 reaction equation
C([N:8]1[CH2:12][CH:11]([CH2:13][CH2:14][OH:15])[CH:10]([CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].CO>[F:29][C:26]1[CH:25]=[CH:24][C:23]([CH:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH:10]3[CH:11]([CH2:13][CH2:14][OH:15])[CH2:12][NH:8][CH2:9]3)[CH2:18][CH2:19]2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70154814HCID 70154814, compound

Product 1

HCID 70154819HCID 70154819, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.89 g (2.3 mmol) of 1-benzyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-hydroxyethylpyrrolidine, 2.9 g (17.7 mmol) of ammonium formate and 0.39 g of Pearlman's catalyst [Pd(OH)2/C] in 30 mL of MeOH was stirred at 70° C. for 1 h. The reaction mixture was filtered through a thin pad of Celite and the filtrate was concentrated to give 0.7 g of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a thin pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6c7f17baf4414f22857017a103ce1645
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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