cis-3-Benzyloxycyclohexan-1-ol → 3-(Benzyloxy)cyclohexanol

HRID 10378Notes

Reaction equation

HRID 10378 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([OH:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC=C)(=O)C.C(Cl)Cl>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([OH:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 10899774cis-3-Benzyloxycyclohexan-1-ol

Product 1

HCID 141727893-(Benzyloxy)cyclohexanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7904Vinyl AcetateSolvent

Procedure

20.3 g of cis-3-benzyloxycyclohexan-1-ol were dissolved in 35 ml of vinyl acetate and 125 ml of methylene chloride, admixed with 2.0 g of Novozym 435 and stirred at 20–23° C. for 6 h. After leaving to stand overnight, the enzyme was filtered off. A sample was withdrawn and concentrated by evaporation under reduced pressure. The enantiomeric excess of (1S,3R)-3-benzyloxycyclohexan-1-ol was >99% (HPLC on Chiralpak AD-H 250×4.6; 1 ml/min, 25:1:0.5 heptane/EtOH/CH3CN+0.1% TFA), and the enantiomeric excess of the (1R,3S)-acetate was 78% (HPLC on Chiralcel OD 250×4.6; 1 ml/min, 100:1:0.5 heptane/EtOH/CH3CN).

Workup

  1. customAfter leaving
  2. waitto stand overnight
  3. filtrationthe enzyme was filtered off
  4. customA sample was withdrawn
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b466e2935dd142b8a4e2dfd6e267d75d
Source dataset
uspto-grants-2006_08
Patent number
US07094795B2

Reaction notes

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