Tetrabutylammonium Fluoride → HCID 86727509, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-3-{1-[4-methyl-3-oxo-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-vinyl}-azetidine-1-carboxylic acid tert-butyl ester (1.214 g, 1.662 mmol) and tetrabutylammonium fluoride (1M in THF, 22.9 mL, 22.9 mmol) was stirred at 80° C. overnight. The reaction was cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0-10% EtOAc in petroleum ether) to give 3-methyl-3-[1-(4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-vinyl]-azetidine-1-carboxylic acid tert-butyl ester (0.330 g, 45%). 1H NMR (CDCl3, 400 MHz): δ 8.25 (s, 1H), 7.35 (s, 1H), 6.66 (s, 1H), 5.46 (s, 1H), 5.15 (s, 1H), 4.7 (m, 2H), 4.6 (m, 1H), 3.95 (m, 1H), 3.86 (m, 1H), 3.65 (m, 2H), 1.55 (m, 3H), 1.50 (m, 3H), 1.40 (s, 9H). LC/MS (Table 1, Method 25) Rt=0.923 min; MS m/z: 503 [M+Na]+.

Provenance & Evidence