Hydrochloric Acid → HCID 86626944, compound

Participants

Reaction Conditions

Reaction Steps

To a vigorously stirred solution of 1-[4-(5-bromopentyloxy)-5-methoxy-2-nitro-benzoyl]-4-methylene-L-proline methyl ester 18 (61 mg, 0.12 mmol) in anhydrous toluene —CH2Cl2 (3:1, 2.5 mL) was added dropwise solution of DIBAL-H (188 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 three drops of methanol followed by 5% HCl (2 mL). The resulting mixture was allowed to warm to 0° C. Layers were separated and the aqueous layer was further extracted with CH2Cl2 (3×2 mL). Combined organic layers were washed with brine, and dried (MgSO4) and concentrated. Purification of the residue by flash chromatography (silica gel, 1:1 hexanes/EtOAc) yielded (S)-1-[4-(5-bromopentyloxy)-5-methoxy-2-nitro-benzoyl]-4-methylene-2-pyrrolidinecarboxaldehyde 19 as light yellow oil (44 mg, 80%).

Provenance & Evidence