Sodium borohydride → HCID 53750662, compound

Participants

Reaction Steps

To a solution of 14 (over 100 mg) in 3 mL of ethanol at 0° was added 45 mg of sodium borohydride. After stirring two hours at 0°, it was quenched with a few drops of acetic acid. Saturated sodium chloride was added, followed by extraction with methylene chloride three times. The combined organic layer was then dried over magnesium sulfate. Removal of the solvent gave 140 mg of 7-[2-(3-hydroxy-1-octen-1-yl)-5-oxopyrrolidin-1-yl]-6-hydroxy-1-heptanoic acid (15). IR (CH2Cl2): 3500-2600 (br), 1720, 1665 cm-1 ; PMR (CDCl3): δ6.33-5.40 (m, 5H, including --CO2H and 2--OH), 4.23-3.00 (m, 5H), 2.66-2.20 (m, 4H), 1.90-1.13 (m, 16H), and 0.93 (t, 3H); MS: m/z 338.2313 (M+ --OH), calcd. for C19H32O4N, 338.2330.

Provenance & Evidence