Reaction #1810795

ord-7ff8bda6f454415db024575f072a4f43

Reaction equation

CCOC(=O)CC(C)O
ethyl 3-hydroxybutyrate
CCOC(=O)CC(O)CBr
ethyl 4-bromo-3-hydroxybutyrate
CCOC(=O)C[C@@H](O)CBr
ethyl (R)-4-bromo-3-hydroxybutyrate
Yield 99.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherAfter reaction for 1 hour 40 minutes

Procedure

Instead of ethyl 3-hydroxybutyrate used in Example 1, ethyl 4-bromo-3-hydroxybutyrate (1%, w/v) was used as a reactant and novozyme 435 lipase was used as a biocatalyst. After reaction for 1 hour 40 minutes, ethyl (R)-4-bromo-3-hydroxybutyrate (99% e.e) was obtained at 88.3% conversion.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07485452B2uspto-grants-2009_02