HCID 58385972, compound → (1S,6R)-6-Amino-2,2-difluorocyclohexanol

HRID 1895879Notes

Reaction equation

HRID 1895879 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 58385972HCID 58385972, compound

Product 1

HCID 58046455(1S,6R)-6-Amino-2,2-difluorocyclohexanolYield 84.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of (1S,6R)-2,2-difluoro-6-{[(1R)-1-phenylethyl]amino}cyclohexanol 23 (2 g, 7.83 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, washing with methanol, and evaporated in vacuo to give 1.0 g (84%) of (1S,6R)-6-amino-2,2-difluorocyclohexanol 24 as a white solid: 1H NMR (500 MHz, CD3OD) δ 3.34 (1H, m), 2.74 (1H, m), 2.07 (1H, m), 1.89 (1H, m), 1.73 (2H, m), 1.50 (1H, m), 1.27 (1H, m).

Workup

  1. filtrationThe reaction was filtered
  2. washwashing with methanol
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-a5c876e577b6426886f5fef099ceba5d
Source dataset
uspto-grants-2013_08
Patent number
US08518911B2

Reaction notes

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