HCID 66671243, compound → HCID 66671028, compound

HRID 2265079Notes

Reaction equation

HRID 2265079 reaction equation
C1(C[N:8]2[CH2:13][CH:12]3[C:10]([C:14]4[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=4)([CH2:11]3)[CH2:9]2)C=CC=CC=1>C(O)C.[Pd]>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([C:10]23[CH2:11][CH:12]2[CH2:13][NH:8][CH2:9]3)=[N:15][CH:16]=1

Participants

4

Reactant 1

HCID 66671243HCID 66671243, compound

Product 1

HCID 66671028HCID 66671028, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(Phenylmethyl)-1-[5-(trifluoromethyl)-2-pyridinyl]-3-azabicyclo[3.1.0]hexane was dissolved in ethanol (15 mL), hydrochloridic acid (3M, 0.76 mL) was added followed, in inert atmosphere, by Pd/C 10% w/w (120 mg). After 20 h under a hydrogen atmosphere (1 atm) the mixture was filtered. Solvent was removed under reduced pressure. A saturated solution of sodium bicarbonate was added (10 mL) and the mixture extracted with diethyl ether (2×10 mL) to provide the title compound (0.14 g, 81%) after evaporation of volatiles.

Workup

  1. filtrationAfter 20 h under a hydrogen atmosphere (1 atm) the mixture was filtered
  2. customSolvent was removed under reduced pressure
  3. additionA saturated solution of sodium bicarbonate was added (10 mL)
  4. extractionthe mixture extracted with diethyl ether (2×10 mL)

Sources & evidence

ORD record
ord-9175af97ce634028a225ef63258b67f1
Source dataset
uspto-grants-2010_12
Patent number
US07855298B2

Reaction notes

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