Dichloromethane → HCID 68294425, compound

Participants

Reaction Steps

A round-bottom flask was charged with (R)-3-amino-3-(3,4-dichlorophenyl)propan-1-ol (9.25 g, 42.0 mmol, CASRN 147611-61-8), DMAP (0.513 g, 4.20 mmol) and DCM (84.1 mL) then a solution of TBDMS-Cl (6.65 g, 44.1 mmol) and DCM (10 mL) was added. The reaction was stirred at RT for 2 d. The reaction mixture was poured into water and extracted with DCM. The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:8 to 500:10) to afford 10.2 g (72%) of (R)-3-(tert-butyl dimethylsilyloxy)-1-(3,4-dichlorophenyl)propan-1-amine (186): m/z (APCI-pos) M+1=334.0.

Provenance & Evidence