Red-Al → HCID 20598111, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 202 (0.504 mmol, 200 mg) in Toluene (2 mL) at 0° C. was treated with 3.0 M Red-Al (3.5 equiv, 1.76 mmol) under Ar. The reaction mixture stirred for 12 h and returned to 25° C. The reaction mixture was then cooled to 0° C., quenched with 10% aqueous NaOH and extracted with EtOAc (3×25 mL). The organics were dried with NaCl(sat) and NA2SO4 (s). The reaction mixture was purified by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, 2:1 hexane-EtOAc) which provided 203 (170 mg, 186 mg theoretical, 91%) as a colorless oil: Rf 0.61 (SiO2, 2:1 hexane-EtOAc); LRMS m/z 368 (M+, C23H29ClN2, requires 368).

Provenance & Evidence