Water → HCID 66706655, compound

Participants

Reaction Steps

Dissolve (R)-(+)-2-(tert-butoxycarbonylamino)-1-propanol (1.75 mg, 10.5 mmol) in anhydrous THF (50 mL). Add sodium hydride (60% in mineral oil, 480 mg, 12 mmol) and stir at 0° C. for 30 min. Add 4-fluorobenzyl bromide (1.5 mL, 12 mmol) followed by tetrabutylammonium iodide (370 mg, 0.1 mmol) and stir for 72 h at ambient temperature. Pour the mixture into water (500 mL), extract with DCM (3×150 mL), wash with brine, dry over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the desired intermediate as a yellow oil (2.18 g, 77%).

Provenance & Evidence