Muskone → (s)-3-Methylcyclopenta-decenyl acetate

HRID 2260930

Reaction equation

HRID 2260930 reaction equation
[C:1]([O:4][C:5]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([CH3:20])[CH:6]=1)(=[O:3])[CH3:2].CC1CCCCCCCCCCCCC(=O)C1>>[C:1]([O:4][C:5]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]([CH3:20])[CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 10947MuskoneHCID 687753723-Methylcyclopentadecene-1-yl acetate

Product 1

HCID 68779586(s)-3-Methylcyclopenta-decenyl acetate

Procedure

Mixed in 20 mL of a phosphate buffer (pH 7) were 2.0 g of dl-3-methylcyclopentadecene-1-yl acetate as obtained in Example 1 (a) and 1.0 g (50 wt. % relative to the substrate) of the immobilized enzyme (Novozyme 435) originating from Candida antarctica, followed by vigorous shaking at 55° C. for 2 days. After the reaction, 20 mL of hexane was added to the reaction solution for extraction, and analysis of the hexane layer showed that the conversion of the substrate was 69.8% and that 3-methylcyclopentadecanone was produced, while 3-methylcyclopentadecene-1-yl acetate remained. The hexane solution was purified by silica-gel column chromatography, and 3-methylcyclopentadecanone, as produced by hydrolyzing a portion of the remained 3-methylcyclopentadecene-1-yl acetate by the conventional method, was subjected to determination of the optical purity by HPLC and identified as the (S) isomer with 90.8% ee of optical purity. Also, 3-methylcyclopentadecanone, a enzymatic hydrolysate of the substrate, was subjected to determination of the optical purity and identified as the (R) isomer with 42.6% ee of optical purity.

Workup

  1. customThe hexane solution was purified by silica-gel column chromatography, and 3-methylcyclopentadecanone
  2. customas produced

Sources & evidence

ORD record
ord-8600619d1cbd49889ca44dfe98058b03
Source dataset
uspto-grants-2010_12
Patent number
US07846701B2

Linked notes

Loading…