Racemic 3-[2-(4-methylphenyl)-5-methyloxazol-4-yl-methoxy]cyclohexan-1-ol → HCID 69657951, compound

HRID 10374Notes

Reaction equation

HRID 10374 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1>C(OC=C)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][O:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([OH:21])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 21980313Racemic 3-[2-(4-methylphenyl)-5-methyloxazol-4-yl-methoxy]cyclohexan-1-ol

Product 1

HCID 69657951HCID 69657951, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 7904Vinyl AcetateSolvent

Procedure

16.3 g of the racemic 3-[2-(4-methylphenyl)-5-methyloxazol-4-yl-methoxy]cyclohexan-1-ol were dissolved in 100 ml of vinyl acetate, admixed with 1.9 g of Chirazyme L-2, lyo., and stirred at 20–23° C. After about 30 minutes, the enzyme was filtered off and the solution concentrated under reduced pressure, crude product: 16.6 g. After chromatography on silica gel (10:1–0:1 n-heptane/ethyl acetate), 8.6 g of (1S,3R)-3-[2-(4-methylphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexan-1-ol and 6.8 g of the (1R,3S)-acetate are obtained.

Workup

  1. filtrationthe enzyme was filtered off
  2. concentrationthe solution concentrated under reduced pressure, crude product

Sources & evidence

ORD record
ord-dbf07741bcdc4e359660bcd6b271e077
Source dataset
uspto-grants-2006_08
Patent number
US07094795B2

Reaction notes

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