HCID 86672013, compound → HCID 67505664, compound

HRID 473829Notes

Reaction equation

HRID 473829 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][F:16])[CH2:12][CH2:11][N:10]2C(OCC2C=CC=CC=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].[H][H]>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][F:16])[CH2:12][CH2:11][NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 86672013HCID 86672013, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67505664HCID 67505664, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (±)-phenylmethyl (2R,4S)-2-(3,4-difluorophenyl)-4-(fluoromethyl)piperidine-1-carboxylate (85 mg, 0.23 mmol), 10% palladium on carbon (85 mg) and ethyl acetate (5 mL) in a 100 mL flask was stirred under 1 atmosphere of hydrogen at room temperature for three days. The mixture was filtered and the filtrate concentrated and dried to give (±)-(2R,4S)-2-(3,4-difluorophenyl)-4-(fluoromethyl)piperidine (39 mg, 73% yield), MS (EI) for C12H14F3N: 230 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customdried

Sources & evidence

ORD record
ord-75d7cc3ed45749c59c1c40626ad8de13
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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