Toluene → HCID 18548816, compound

Participants

Reaction Steps

To a stirred suspension of 2-[3-(4-oxo-7-pyrrol-1-yl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-phenyl]-thiazole-4-carboxylic acid ethyl ester (Example 19) (0.34 g, 0.75 mmol) in THF (35 mL) was added at −20° C. over 40 min in 3 portions a 3.5 M solution of sodium dihydrido-bis(2-methoxyethoxy)aluminate in toluene (0.94 mL, 3.3 mmol). Stirring was continued at −20° C. for 20 min. and the reaction mixture was then poured into ice-cold 10% aqueous acetic acid. The product was extracted with EtOAc and the organic layer was washed successively with H2O, sat. Na2CO3-solution and brine, dried over Na2SO4 and evaporated in vacuum. The residue was triturated with methanol to give the title compound (0.28 g) as light-yellow solid.

Provenance & Evidence