Methyl 2-(cis-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate → methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate

HRID 1373161Notes

Reaction equation

HRID 1373161 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH2:3]1>C(OC=C)(=O)C>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH2:3]1

Participants

3

Reactant 1

HCID 69207297Methyl 2-(cis-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate

Product 1

HCID 11492838methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 7904Vinyl AcetateSolvent

Procedure

8 g of methyl 2-(cis-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate are dissolved in 100 ml of vinyl acetate, and 1 g of Candida antartika lipase B is added. The mixture is stirred at room temperature for seven hours and the enzyme is then filtered off and the solvent is removed under reduced pressure. The residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=10:1). This gives 3.9 g of the alcohol methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate as a colorless oil. C16H22O4 (278.35), MS(ESI): 279 (M+H+), ee=98% (Chiralpak AD/2 250×4.6; n-heptane:ethanol:methanol=25:1:0.5+0.1% trifluoroacetic acid, Rt=8.9 min; retention time of the enantiomer: Rt=9.9 min).

Workup

  1. addition1 g of Candida antartika lipase B is added
  2. filtrationthe enzyme is then filtered off
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-0a4e0c02ff2449fe89d5a22611451c2e
Source dataset
uspto-grants-2007_01
Patent number
US07160911B2

Reaction notes

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