Propanal → HCID 10224846, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (+)-[8-bromo-9-[(4-chlorophenyl)sulfanyl]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid (Example 7A, 700 mg, 1.5 mmol) in THF (15 mL) at −78° C. was added 3M MeMgBr in THF (1.9 mmol) followed by the addition of 1.6M nBuLi in hexane (3.1 mmol). The reaction mixture was stirred at −78° C. for 2 minutes and an excess of propionaldehyde was added. The reaction mixture was stirred at −78° C. for 15 minutes, warmed to r.t and quenched with saturated aqueous NH4Cl The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with EtOAc/hexanes/AcOH (20:30:1) to provide the title compound as a white solid.

Provenance & Evidence