(S)-methyl 6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoate → (S)-methyl 2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-6-hydroxyhexanoate

HRID 1643291Notes

Reaction equation

HRID 1643291 reaction equation
C([O:8][CH2:9][CH:10]=[CH:11][CH2:12][C@@H:13]([CH2:18][C@H:19]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[O:20][CH3:21])[C:14]([O:16][CH3:17])=[O:15])C1C=CC=CC=1.[H][H]>[Pd].CCO>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C@H:19]([O:20][CH3:21])[CH2:18][C@H:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[C:14]([O:16][CH3:17])=[O:15])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 66754419(S)-methyl 6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 59568820(S)-methyl 2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-6-hydroxyhexanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(S)-methyl 6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hex-4-enoate (494 mg, 1.2 mmol) was dissolved into 5 mL EtOH and to it added 10% Pd/C (450 mg). The solution was saturated with H2 (stream of H2 bubbled through solution) and then stirred for 3 h at room temperature under one atmosphere of hydrogen (balloon). The mixture was filtered through a bed of Celite and rinsed with ethyl acetate. The solvent was removed under reduced pressure and the crude product used directly in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. washrinsed with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product used directly in the next step without further purification

Sources & evidence

ORD record
ord-f2dc1b3350064532aa16af9c812459ea
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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