Sodium hydride → HCID 86649378, compound

Participants

Reaction Steps

Charge a vial with (S)-benzyl 7,9-dimethyl-5-(2-methyl-2H-tetrazol-5-ylamino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate (100 mg 246 μmoles), NaH (23 mg 60% in mineral oil, 575.1 μmoles) and THF (9.2 ml, 24.6 mmoles). (Alternatively, potassium tert-butoxide in DMF can be used in place of NaH and THF.) Stir the reaction mixture at RT for 10 m. Add 3,5 bis(trifluoromethyl)benzylbromide (173.8 mg 566.2 μmoles) dropwise over 30 min. After about 19 h, add NaH (10 mg, 60% mineral oil) and stir for an additional 1 h. Partition the reaction mixture between EtOAc (50 mL) and brine (2×25 mL). Collect the organic layers and dry over Na2SO4. Filter and then concentrate the filtrate to yield an oil. Partition the oil between ACN (50 mL) and heptane (2×25 mL). Collect the CAN layer; dry to yield an oil (189 mg) of the title compound.

Provenance & Evidence