Phenylacetaldehyde → HCID 67511755, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of D-proline (2.93 g), N-ethyl-diisopropylamine (4.36 mL) in toluene (70 mL) was added 2-cyclohexen-1-one (10 mL) and phenyl acetaldehyde (14.6 mL) at 20-25° C. The mixture was stirred for 3 d at 45° C. IPC according to LC-MS method 1 indicated>99% conversion. The suspension was cooled to 20-25° C. and filtered. The filter cake was washed with water (3×10 mL), followed by toluene wash (3×10 mL). The filter cake was dried on the filter by sucking air through the filter. Yield: 13.2 g, 60%. 1H-NMR (CDCl3) corresponds to structure of compound ent-2. Chiral HPLC method:enantiomeric ratio=27:73 (2:ent-2), diastereomeric purity: 100%; LC-MS method 1: 100% a/a, tR=1.19.

Provenance & Evidence