Hydrochloric Acid → HCID 11760910, compound

Participants

Reaction Steps

To a solution of 6-tert-butyldiphenylsilyloxy-1-indanone, as described above in Step A, (16.5 g, 42.7 mmol) in MeOH (500 mL) was added NaBH4 (3.2 g, 84.6 mmol) portionwise, over 5 min. The resulting mixture was stirred at ambient temperature for 1 hour, then cooled to 0° C. The chilled solution was adjusted to pH 4.5 with dilute aqueous HCl, then most of the MeOH was removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (75 mL) and CHCl3 (150 mL). The organic layer was removed, and the aqueous phase was extracted further with CHCl3 (2×100 mL). The combined organic extracts were washed with brine, then dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with hexane—10% to EtOAc, to yield the titled product.

Provenance & Evidence