Tetrabutylammonium Fluoride → Benzyl 3-hydroxypropylmethylcarbamate

Participants

Reaction Steps

TBAF (12.8 ml, 1.0 M solution in THF, 12.8 mmol) was added to the solution of benzyl 3-(tert-butyldimethylsilyloxy)propyl(methyl)carbamate obtained in step 3 (3.6 g, 10.7 mmol) in THF (30 ml). After reaction complete, water and EtOAC work-up and then drying were followed to give benzyl 3-hydroxypropyl(methyl)carbamate (formula 31). After further purification, alcohol was treated with triphenylphosphine (3.35 g, 12.8 mmol) and carbon tetrabromide (12.8 mmol) in acetonitrile (20 ml). The reaction progress was monitored by TLC or LS/MS. After reaction complete, the organic layer was extracted and evaporated. The residue was purified with silica gel column chromatography (EtOAC:Hx=1:5) to give the title compound (2.5 g, 82%, 2 steps) as light yellow oil.

Provenance & Evidence