Diethyl Ether → HCID 21896696, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution (−78° C.) of 1,1-dioxo-2-(4-methoxybenzyl)-3,3dibutyl-5-phenyl-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 23; 2.10 g, 3.41 mmol) in THF (50 ml) was added dropwise a solution of n-BuLi (2.35 ml, 3.75 mmol, 1.6 M in hexane). After stirring at −78° C. for 20 minutes, MeI (2.42 g, 17.1 mmol) was added. The mixture was stirred at −78° C. for 10 minutes and at room temperature for 18 hours. Diethyl ether (50 ml) was added and the organic phase was washed with 10% NH4Cl (aq, 50 ml) and brine (50 ml). After drying, filtration and concentration the crude product was subjected to flash chromatography (Hexane:EtOAc—95:5) to give 0.4 gram (21%) of the title product as colourless oil. NMR (300 MHz, CDCl3): 0.60–0.70 (m, 6H), 0.70–0.90 (m, 4H), 0.90–1.35 (m, 8H), 2.00 (s, 3H), 3.70 (s, 3H), 3.80 (s, 3H), 4.00–4.20 (m, 2H), 4.35–4.60 (m, 2H), 6.65–6.85 (m, 3H), 6.90–7.10 (m, 3H), 7.15–7.30 (m, 5H).

Provenance & Evidence