HCID 57496387, compound → HCID 57496388, compound

HRID 537740Notes

Reaction equation

HRID 537740 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][CH2:5][CH:4]([C@@H:8]2[CH2:13][C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:10][N:9]2C(OCC2C=CC=CC=2)=O)[CH2:3]1.[H][H]>CCO.[OH-].[OH-].[Pd+2]>[F:30][C:2]1([F:1])[CH2:7][CH2:6][CH2:5][CH:4]([C@@H:8]2[CH2:13][C@H:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:11][CH2:10][NH:9]2)[CH2:3]1

Participants

5

Reactant 2

HCID 57496387HCID 57496387, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57496388HCID 57496388, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 11 (500 mg, 1.2 mmol) and Pd(OH)2 (0.2 g) in 10 ml of EtOH was hydrogenated under 1 atmosphere of hydrogen at room temperature overnight. Filtration and concentration afforded (2S,4R)-2-(3,3-difluorocyclohexyl)-4-phenylpiperidine as a colorless oil (330 mg, 98%).

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-1db2a1904ed74bbbba8cb25ae8430ddd
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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