Formic Acid → ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (830 mg, 8.20 mmol) and formic acid (227 mg, 4.93 mmol) were added to a chlorobenzene solution (15.0 ml) of RuCl[(R,R)-TsDPEN](p-cymene) complex (11.0 mg, 0.03 mmol) and ethyl 2-octadecanoylamino-3-oxooctadecanoate (1.00 g, 1.64 mmol) synthesized in the same method as Example 10. After the reaction mixture was stirred for 3 days at 40° C., water (10 mL) was added thereto and separation operation was carried out at 40° C. to obtain the organic layer. After the organic layer was concentrated until the total amount became 3.11 g, 10 mL of AcOEt was added thereto and recrystallization was carried out to obtain 0.73 g of the title compound (yield: 74%). Anti-form:syn-form was 100:0 and the optical purity of the anti-form was 100% ee.

Provenance & Evidence