Ethyl formate → HCID 19771747, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-ethyl-5,6,7,8-tetrahydro-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,6-naphthyridine (500 mg) in dry tetrahydrofuran (THF) (2 ml) was added dropwise over a period of 20 minutes to a stirred suspension of lithium aluminium hydride (116 mg) in dry THF (2 ml) under an atmosphere of argon. The mixture was cooled to 0° C. and ethyl formate (173 mg) was added dropwise over a period of 10 minutes. The mixture was stirred for 1 hour and then water (0.12 ml), 4M sodium hydroxide solution (0.12 ml) and water (0.36 ml) were added successively. Stirring was continued for 10 minutes, and then insoluble material was removed by filtration and washed with ether (50 ml). The combined filtrate and washings were evaporated to dryness and the residue purified by flash chromatography, eluting with a mixture of methanol and dichloromethane (1:9 v/v). to give 2-ethyl-6-methyl-5,6,7,8-tetrahydro-4-[ (2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)-methoxy]-1,6-naphthyridine (240 mg), as a pale yellow solid, m.p. 143°-144° C.; NMR (d6 -DMSO, d4 -acetic acid): 1.2(t,3H), 2.65(q,2H), 2.95(s,4H), 3.65(s,2H), 5.15(s,2H), 6.8-6.9(m,7H), 7.1(d,2H), 7.3-7.7 (complex m,14H), 7.85(dd,1H).

Provenance & Evidence