HCID 13296325, compound → HCID 71230571, compound

HRID 401844Notes

Reaction equation

HRID 401844 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@@H:16]1[C@@H:21]([CH3:22])[CH2:20][C:19]([CH3:23])=[CH:18][CH2:17]1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@H:16]1[CH2:17][CH2:18][C@H:19]([CH3:23])[CH2:20][C@@H:21]1[CH3:22])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 13296325HCID 13296325, compound

Product 1

HCID 71230571HCID 71230571, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-4-benzyl-3-((1S,6S)-4,6-dimethylcyclohex-3-enecarbonyl)oxazolidin-2-one (6 g, 19.1 mmol) and 10% Pd/C (500 mg) in EtOH (50 mL) under a H2 atmosphere (1 atm) was stirred at room temperature overnight. The reaction mixture was filtered through a pad of diatomaceous earth and concentrated to give a 3:1 mixture of diastereomers, which were separated by preparative chiral column chromatography (Chiralcel OD-H (20 cm×250 cm; semi prep): Retention time: 24 min, 33 min (major) (80:20 heptane:ethanol)), providing (S)-4-benzyl-3-((1S,2S,4S)-2,4-dimethylcyclohexanecarbonyl)oxazolidin-2-one (2.3 g, 38%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. concentrationconcentrated
  3. customto give
  4. additiona 3:1 mixture of diastereomers, which
  5. customwere separated by preparative chiral column chromatography (Chiralcel OD-H (20 cm×250 cm; semi prep): Retention time: 24 min, 33 min (major) (80:20 heptane:ethanol))

Sources & evidence

ORD record
ord-91c318923a784c41afa66d1fc517379b
Source dataset
uspto-grants-2014_06
Patent number
US08741946B2

Reaction notes

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