Reaction #10475

Reaction equation

cis-3-benzyloxycyclohexan-1-ol

→

3-benzyloxycyclohexan-1-ol

Solvents

vinyl acetate

methylene chloride

Conditions

Workup

1. 1
   FiltrationThe enzyme was filtered off
2. 2
   Othera sample was withdrawn
3. 3
   Concentrationconcentrated by evaporation under reduced pressure

Procedure

100.0 g of cis-3-benzyloxycyclohexan-1-ol were dissolved in 170 ml of vinyl acetate and 630 ml of methylene chloride, admixed with 5.0 g of Novozym 435 and stirred at 20–23° C. for 26 h. The enzyme was filtered off, and a sample was withdrawn and concentrated by evaporation under reduced pressure.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 90% (HPLC on Chiralcel OD 250×4.6; 1 ml/min, 100:1:0.5 heptane/EtOH/CH3CN).

Source