HCID 22088819, compound → HCID 22088823, compound

HRID 2227894Notes

Reaction equation

HRID 2227894 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]2[O:22][C:17]2([O:23][CH3:24])[C:18]([F:21])([F:20])[F:19])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]2[O:22][C:17]2([O:23][CH3:24])[C:18]([F:19])([F:20])[F:21])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 22088819HCID 22088819, compound

Product 1

HCID 22088823HCID 22088823, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S*, 3R*)-4-(4-benzyloxyphenyl)-2-methoxy-1,1,1-trifluoro-2,3-epoxy-butane (957 mg, 2.8 mmol) in ethyl acetate (30 ml) was hydrogenated at atmospheric pressure over palladium hydroxide/carbon (20%, 290 mg) for 1 hour. The mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated in vacuo and chromatographed on silica gel (hexane:ethyl acetate=7:1-5:1) to give the title compound (691 mg, 97%) as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed on silica gel (hexane:ethyl acetate=7:1-5:1)

Sources & evidence

ORD record
ord-3594747c9ce9464db3fc48bde2b88530
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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