HCID 12772862, compound → HCID 11126946, compound

HRID 1376255Notes

Reaction equation

HRID 1376255 reaction equation
[O:1]1[CH:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:2]1[C:3]([O:5][CH3:6])=[O:4]>C1(C)C=CC=CC=1>[O:1]1[C@H:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C@H:2]1[C:3]([O:5][CH3:6])=[O:4]

Participants

3

Reactant 1

HCID 12772862HCID 12772862, compound

Product 1

HCID 11126946HCID 11126946, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

500 ml of toluene containing 100 g of methyl 2,3-epoxy-3-cyclohexylpropionate, was added to 500 ml of a 1M tris-HCl buffer solution (pH 8.0) containing lipase (derived from hog pancreas, manufactured by Wako Pure Chemical Industries, Ltd.) in a concentration of 5 g/l, and asymmetric hydrolysis reaction was carried out at 30° C. for 48 hours at a stirring speed of 600 rpm. After the reaction, the toluene phase was separated and concentrated under reduced pressure to obtain 25.2 g of a crude product of methyl (2S,3R)-2,3-epoxy-3-cyclohexylpropionate as a colorless oil substance. By purification by silica gel chromatography (hexane/ethyl acetate=9/1 (v/v)), 23.0 g of methyl (2S,3R)-2,3-epoxy-3-cyclohexylpropionate was obtained (98.6% ee [α]D20=+32.6 (c 1.18, CHCl3)).

Workup

  1. additioncontaining lipase (derived from hog pancreas, manufactured by Wako Pure Chemical Industries, Ltd.)
  2. customin a concentration of 5 g/l, and asymmetric hydrolysis reaction
  3. customAfter the reaction
  4. customthe toluene phase was separated
  5. concentrationconcentrated under reduced pressure
  6. customto obtain 25.2 g of a crude product of methyl (2S,3R)-2,3-epoxy-3-cyclohexylpropionate as a colorless oil substance
  7. customBy purification by silica gel chromatography (hexane/ethyl acetate=9/1 (v/v))

Sources & evidence

ORD record
ord-6dc93ed89200451188cb4903418a6c75
Source dataset
uspto-grants-2007_01
Patent number
US07169944B2

Reaction notes

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