Reaction #1810794

ord-db7f65637b054d018429f55febfd6198

Reaction equation

CCOC(=O)CC(C)O
ethyl 3-hydroxybutyrate
CCOC(=O)CC(O)CN=[N+]=[N-]
ethyl 4-azido-3-hydroxybutyrate
→
CCOC(=O)C[C@H](O)CN=[N+]=[N-]
ethyl (S)-4-azido-3-hydroxybutyrate
Yield 80.2%

Reactants

CCOC(=O)CC(C)O
ethyl 3-hydroxybutyrate
CCOC(=O)CC(O)CN=[N+]=[N-]
ethyl 4-azido-3-hydroxybutyrate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Instead of ethyl 3-hydroxybutyrate used in Example 1, ethyl 4-azido-3-hydroxybutyrate was used. The reaction was carried out for 1 hour and ethyl (S)-4-azido-3-hydroxybutyrate (80.2% e.e) was obtained at 83.5% conversion.

Source

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