HCID 86656432, compound → HCID 67352034, compound

HRID 1895884Notes

Reaction equation

HRID 1895884 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]1([F:25])[CH2:14][CH2:13][CH2:12][C@H:11]([OH:15])[C@H:10]1[NH2+:16][C@@H](C1C=CC=CC=1)C.[H][H]>[Pd].CO>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]1([F:25])[CH2:14][CH2:13][CH2:12][C@H:11]([OH:15])[C@H:10]1[NH3+:16]

Participants

5

Reactant 2

HCID 86656432HCID 86656432, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67352034HCID 67352034, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1R,6S)-2,2-difluoro-6-hydroxy-N-[(1R)-1-phenylethyl]cyclohexanaminium trifluoroacetate (74) in a solution of methanol (1.5 mL) was exposed to Pd/C (409 mg, 0.384 mmol) and hydrogen atmosphere (1 atm). The heterogeneous reaction mixture was filtered through a plug of celite and washed three times with 30 mL of methanol. The filtrate was concentrated under reduced pressure to yield (1R,6S)-2,2-difluoro-6-hydroxycyclohexanaminium trifluoroacetate (75) in quantitative yield. 1H NMR (500 MHz, CD3OD) δ 3.68 (s, 1H), 3.34 (t, J=16.6, 2H), 2.19 (s, 1H), 2.06 (s, 1H), 1.87 (d, J=56.3, 2H), 1.49 (s, 2H), 19F NMR (470 MHz, cd3od) δ −77.30 (s, 3F), −99.95 (d, J=242.9, 1F), −114.48-−116.71 (m, 1F).

Workup

  1. filtrationThe heterogeneous reaction mixture was filtered through a plug of celite
  2. washwashed three times with 30 mL of methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9dd9d06780a24d189f0fc25a16ce3ce2
Source dataset
uspto-grants-2013_08
Patent number
US08518911B2

Reaction notes

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