반응 #350562

ord-0c5496e721c64d32bc29ca395a6a7767

반응 방정식

CCCCOC(=O)CC(O)CCC
racemic butyl 3-hydroxyhexanoate
CCCC(O)CC(=O)OCc1ccccc1
racemic benzyl 3-hydroxyhexanoate
CCC[C@@H](O)CC(=O)OC
(R)-methyl 3-hydroxyhexanoate
수율 36.0%
CCC[C@H](O)CC(=O)OCc1ccccc1
(S)-benzyl 3-hydroxyhexanoate
수율 40.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타obtained in Reference example 3
  2. 2
    기타The resulting mixture was reacted
  3. 3
    workup.STIRRINGwith stirring
  4. 4
    여과The steps from filtration of the lipase to chromatograph with a silica gel column

실험 절차

The same procedure was repeated except that racemic butyl 3-hydroxyhexanoate was changed into the racemic benzyl 3-hydroxyhexanoate 1.0 g (4.5 mmol) obtained in Reference example 3 and stirring time was changed into nine hours. The resulting mixture was reacted with stirring. After the reaction was stopped, the conversion of 52% was determined. The steps from filtration of the lipase to chromatograph with a silica gel column were conducted as shown in Example 1 to obtain (R)-methyl 3-hydroxyhexanoate 0.24 g (1.6 mmol, 36%) and (S)-benzyl 3-hydroxyhexanoate 0.40 g (1.8 mmol, 40%). Optical purity of these compounds was determined by HPLC. The optical purity of the (R)-compound was 88% ee and that of the (S)-compound was 96% ee.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05643793uspto-grants-1997_07