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

HRID 1353164Notes

Reaction equation

HRID 1353164 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

13.1 g of methyl cis-2-(3-hydroxycyclohexyloxymethyl)-6-methylbenzoate are dissolved in 100 ml of vinyl acetate and 1.6 g of Candida antartika lipase B are added. After eight hours of stirring at room temperature, the enzyme is 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→ethyl acetate). This gives 4.3 g of methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate as a colorless oil. C16H22O4 (278.35), MS(ESI): 279 (M+H+), ee=99% (Chiralpak AD/2 250×4.6; n-heptane:ethanol:methanol=25:1:0.5+0.1% trifluoroacetic acid, Rt=8.9 min)

Workup

  1. addition1.6 g of Candida antartika lipase B are added
  2. filtrationthe enzyme is 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→ethyl acetate)

Sources & evidence

ORD record
ord-c848c2d117a74b2f9c379a2898c65ecf
Source dataset
uspto-grants-2007_05
Patent number
US07220876B2

Reaction notes

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