2-Morpholinoethanol → HCID 131729101, compound

Participants

Reaction Steps

Following the general procedure for the preparation of carboxylic esters from carboxylic acids of Description 15, (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoic acid (14) (0.5 g, 1.2 mmol) dissolved in 5 mL of anhydrous dichloromethane (DCM) was reacted with 0.14 mL (0.2 g, 0.14 mmol) of oxalyl chloride. After completion of the reaction, a solution of 0.37 g (2.8 mmol) of 2-morpholin-4-yl ethanol in anhydrous dichloromethane (DCM) was added to the acid chloride. After work-up, the crude material was purified by silica gel column chromatography using ethyl acetate as eluent to provide 0.22 g (35% yield) of the title compound (27a) as a colorless oil. Rf=0.67 (EtOAc). 1H NMR (400 MHz, CDCl3): δ=1.07 (s, 3H), 1.09 (s, 3H), 2.26-2.32 (m, 2H), 2.53-2.70 (m, 6H), 3.22-3.26 (m, 2H), 3.65-3.69 (m, 6H), 3.82 (s, 3H), 3.84 (s, 1H), 4.02 (d, J=9.2 Hz, 1H), 4.19 (d, J=8.8 Hz, 1H), 4.30-4.38 (m, 3H), 4.59 (d, J=9.2 Hz, 1H), 6.88 (d, J=7.2 Hz, 2H), 7.27 (d, J=6.8 Hz, 2H) ppm. MS (ESI) m/z 529.09 (M+H)+.

Provenance & Evidence