Ethanol → HCID 6355768, compound

HRID 401846Notes

Reaction equation

HRID 401846 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.CC[OH:26]>[Pd]>[CH3:22][C@@H:21]1[CH2:20][C@H:19]([CH3:23])[CH2:18][CH2:17][C@H:16]1[C:14]([OH:15])=[O:26].[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

5

Reactant 2

HCID 702EthanolHCID 71230542HCID 71230542, compound

Product 2

HCID 6355768HCID 6355768, compoundHCID 71230563HCID 71230563, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (R)-4-benzyl-3-((1R,6R)-4,6-dimethylcyclohex-3-ene-carbonyl)oxazolidin-2-one (1.5 g, 4.8 mmol) (J. Am. Chem. Soc. 110(4), 1988, 1238-1256) in EtOH (24 mL) and 10% Pd/C (500 mg) was stirred under a H2 atmosphere (1 atm) 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: Chiral-Pak AD-H (20 cm×250 cm; semi prep): Retention time: 5.11 min, 6.25 min (80:20 heptane:ethanol), providing the desired compound (R)-4-benzyl-3-((1R,2R,4R)-2,4-dimethylcyclohexanecarbonyl)oxazolidin-2-one (0.65 g).

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

Sources & evidence

ORD record
ord-e0d8ee884ca34340bd42de0437f0a5b5
Source dataset
uspto-grants-2014_06
Patent number
US08741946B2

Reaction notes

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