Benzyl 3-hydroxyhexanoate → HCID 10822918, compound

HRID 263380Notes

Reaction equation

HRID 263380 reaction equation
[OH:1][CH:2]([CH2:11][CH2:12][CH3:13])[CH2:3][C:4]([O:6][CH2:7]CCC)=[O:5].[OH:14][CH:15]([CH2:27][CH2:28][CH3:29])[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>>[OH:1][C@H:2]([CH2:11][CH2:12][CH3:13])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[OH:14][C@@H:15]([CH2:27][CH2:28][CH3:29])[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]

Participants

4

Reactant 2

HCID 15188750Benzyl 3-hydroxyhexanoateHCID 19037310HCID 19037310, compound

Product 2

HCID 10822918HCID 10822918, compoundYield 40%HCID 13617479HCID 13617479, compoundYield 36%

Procedure

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.

Workup

  1. customobtained in Reference example 3
  2. customThe resulting mixture was reacted
  3. stirringwith stirring
  4. filtrationThe steps from filtration of the lipase to chromatograph with a silica gel column

Sources & evidence

ORD record
ord-0c5496e721c64d32bc29ca395a6a7767
Source dataset
uspto-grants-1997_07
Patent number
US05643793

Reaction notes

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