Tetrabutylammonium Fluoride → HCID 86727611, compound

Participants

Reaction Conditions

Reaction Steps

(2S,5R)-4-[7-(2-Fluoro-phenyl)-4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (0.2 g, 0.306 mmol) was dissolved in tetrabutylammonium fluoride (1M in THF, 3.06 mL, 3.06 mmol) and the reaction mixture was heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature and water (10 mL) was added. The reaction mixture was extracted with EtOAc (3×10 mL). The combined organic phase was washed with brine (3×10 mL) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0-40% EtOAc in petroleum ether) to give (2S,5R)-4-[7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (0.112 g, 70%) as a solid. LC/MS (Table 1, Method 25) Rt=0.959 min.; MS m/z: 524 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.15-8.08 (m, 1H), 7.42 (m, 1H), 7.35-7.29 (m, 1H), 7.22-7.10 (m, 2H), 6.95-6.91 (m, 1H), 6.52-6.46 (m, 1H), 4.76-4.72 (m, 1H), 4.65-4.54 (m, 2H), 4.35 (m, 1H), 3.45 (m, 1H), 3.33 (m, 1H), 2.85 (m, 1H), 2.69 (m, 1H), 2.60 (m, 1H), 1.52 (m, 3H), 1.49-1.32 (m, 9H), 1.24 (m, 3H), 0.81 (m, 3H).

Provenance & Evidence