Hydrochloric Acid → HCID 86626942, compound

Participants

Reaction Conditions

Reaction Steps

To a vigorously stirred solution of bis{2-[5-methoxy-2-nitro-4-[(S)-4-methylene-2-methoxycarbonyl-1-pyrrolidinylcarbonyl]phenyloxy]-ethyl}-carbamic acid tert-butyl ester 12 (100 mg, 0.12 mmol) in anhydrous toluene (2.4 mL) was added dropwise solution of DIBAL-H (480 μL of a 1M solution in toluene) at −78° C. under argon atmosphere. After the mixture was stirred for an additional 45 min, excess reagent was decomposed by addition of five drops of methanol followed by 5% HCl (4 mL). The resulting mixture was allowed to warm to 0° C. Layers were separated and the aqueous layer was further extracted with CH2Cl2 (3×3 mL). Combined organic layers were washed with brine, dried (MgSO4) and concentrated. Purification of the residue by flash chromatography (silica gel, 95:5 CHCl3/MeOH) yielded bis{2-[5-methoxy-2-nitro-4-[(S)-4-methylene-2-formyl-1-pyrrolidinylcarbonyl]phenyloxy]-ethyl}-carbamic acid tert-butyl ester 13 as light yellow oil (84 mg, 91%).

Provenance & Evidence