Hydrochloric Acid → HCID 21480498, compound

Participants

Reaction Steps

To a solution of the product from Step C (8.77 g, 23.4 mmol) in anhydrous ether (100 mL) at 0° C. was added diisobutylaluminium hydride (1M solution in hexanes, 70.2 mmol). The reaction mixture was stirred for 1 h, a solution of potassium sodium tartrate (28.2 g in 100 mL water) was added, and the resulting mixture stirred for 2 h. The aqueous layer was separated and extracted with ethyl acetate (2×100 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to give an oil which was dissolved in acetone (100 mL) and treated with 100 mL of 2 N HCl for 4 h. The acetone was evaporated and the remaining aqueous mixture was extracted with ethyl acetate (2×100 mL) The combined extracts was dried and evaporated to give a solid (4.82 g, 79%); Recrystallization from EtOAc/Hex gave a crystalline solid: mp 81°-83° C.

Provenance & Evidence