Hydrochloric Acid → HCID 86670075, compound

Participants

Reaction Conditions

Reaction Steps

To a suitable reactor was added 3c (2.2 g, 1.0 eq) and EtOH (11 mL) at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (304.1 mg, 0.8 equiv) in H2O (4 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 complete as determined by TLC. 1N HCl aqueous solution (32 mL) was added at below 10° C., and the mixture was warmed to 20-30° C. EtOAc (200 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 4c. The diastereomeric ratio of crude 4c was determined to be 64/36 by HPLC analysis. The residue was purified by flash column chromatography (EtOAc/n-heptane=1/2) to give a diastereomeric mixture of 4c (2.20 g, 83% yield) as a yellow solid.

Provenance & Evidence