Tetrabutylammonium Fluoride → HCID 86701111, compound

Participants

Reaction Steps

A solution of tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate (1.36 g, 2.06 mmol) in THF (30 mL) was treated with tetrabutylammonium fluoride (1.1 g, 4.2 mmol) for 2 hrs at room temperature. The reaction mixture was quenched with H2O (10 mL), extracted with ethyl acetate (3×50 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 10%-20% ethyl acetate in petroleum ether to provide compound 71 as a pale yellow oil (600 mg, 53%). (ES, m/z) [M+H]+ 546.8; 1H NMR (300 MHz, CDCl3) δ 7.24-7.43 (m, 10H), 6.09-6.11 (d, J=4.2 Hz, 1H), 4.60-4.66 (m, 2H), 4.50-4.54 (m, 1H), 4.46-4.47 (m, 1H), 4.40-4.45 (m, 2H), 4.27-4.39 (m, 2H), 4.12-4.22 (m, 2H), 3.72-3.79 (m, 1H), 3.67-3.71 (m, 1H), 3.55-3.63 (m, 1H), 3.40-3.45 (m, 1H), 1.54 (s, 9H).

Provenance & Evidence