HCID 58046435, compound → (1S,6R)-6-Amino-2,2-difluorocyclohexanol

HRID 2046396Notes

Reaction equation

HRID 2046396 reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C@@H](C2C=CC=CC=2)C)[C@@H:3]1[OH:17]>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:4]1[C@H:3]([OH:17])[C:2]([F:18])([F:1])[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 58046435HCID 58046435, compound

Product 1

HCID 58046455(1S,6R)-6-Amino-2,2-difluorocyclohexanol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of (1S,6R)-2,2-difluoro-6-{[(1R)-1-phenylethyl]amino}cyclohexanol (2.0 g, 7.8 mmol) in methanol (100 mL) was degassed with nitrogen, treated with Pd(OH)2/C (0.55 g) and then placed under an atmosphere of hydrogen and stirred vigorously for 16 hours. The reaction was filtered, washed with methanol, and the filtrate evaporated in vacuo to afford the title compound as a white solid: 1H NMR (500 MHz, CD3OD) δ 3.34 (m, 1H); 2.74 (m, 1H); 2.07 (m, 1H); 1.89 (m, 1H); 1.73 (m, 2H); 1.50 (m, 1H); 1.27 (m, 1H).

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with methanol
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-5948e9a9a313489b988619dd75daa21c
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Reaction notes

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