Hydrochloric Acid → HCID 86670077, compound

Participants

Reaction Conditions

Reaction Steps

To a suitable reactor was added 3e (1.32 g, 1.0 equiv) and EtOH (26 mL) at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (117.4 mg, 0.8 equiv) in H2O (2.6 mL) was added at below −15° C. The reaction mixture was warmed to −5-5° C. and stirred for 1 hr. The reaction was deemed completed as determined by TLC. 1N HCl aqueous solution (13 mL) was added at below 10° C., and the mixture was warmed to 20-30° C. EtOAc (160 mL) was added at 20-30° C., and the mixture was stirred at this temperature for 30 min. The separated organic portion was concentrated at 40-50° C. under reduced pressure to afford crude 4e. The diastereomeric ratio of crude 4e was determined to be 78/22 by HPLC analysis. The residue was purified by flash column chromatography (EtOAc/n-heptane=1/2) to give a diastereomeric mixture of 4e (0.92 g, 81% yield) as a yellow oil.

Provenance & Evidence