(Dimethyl sulfide)trihydroboron → HCID 86756029, compound

Participants

Reaction Steps

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-methoxy-7-(1-methoxycarbonyl-cyclopentyl)-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 27) (700 mg; 1.04 mmol) in 20 mL anhydrous tetrahydrofuran was added borane-dimethylsulfide complex (1M THF; 2.28 mL) and the reaction was heated to reflux for 3 hours. The reaction was quenched with H2O and extracted with 50 mL of ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated. The residue was chromatographed (25% ethyl acetate-hexane) to afford the title product (20 mg). MS m/z 664 (M++18); 1H NMR (CDCl3) δ 1.1 (d, 3H), 3.6 (s, 2H), 3.7 (s, 3H), 3.8 (s, 3H), 6.3 (S, 1H), 7.3 (S, 1H), 7.7 (S, 2H), 7.8 (S, 1H).

Provenance & Evidence