Hydrochloric Acid → HCID 66934433, compound

Participants

Reaction Conditions

Reaction Steps

The product of step (d) (mixture of diastereomers, 234 mg, 1.54 mmol) was dissolved in 5 mL EtOH and treated with NaBH4 (117 mg, 3.1 mmol). After stirring for 15 minutes, the reaction was quenched with HOAc and diluted with water (10 mL). The product was extracted into DCM (2×25 mL) and the extracts were concentrated to dryness. The crude residue was dissolved in HOAc (8 mL) and concentrated HCl (4 mL) and treated with SnCl2 (1.4 g, 6.2 mmol). After heated to 80° C. for 1 hour, the reaction was cooled and diluted with water (15 mL). The product was extracted into DCM (3×25 mL) and the extracts were dried over MgSO4 and concentrated to dryness. The diastereomers were separated by HPLC (Novapak C-18, 19×300 mm, 55% CH3CN/water, 10 mL/min) to give diastereomer 1 (rt=23.0 min) and diastereomer 2 (rt=24.2 min) giving approximately 20 mg of each diastereomer.

Provenance & Evidence