Triethylamine → 3-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl ester

Participants

Reaction Steps

A solution of [2-(3-bromophenyl)-1,1-dimethylethyl]carbamic acid tert-butyl ester (Preparation 32) (7.0 g, 21 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.74 g, 2.1 mmol) and triethylamine (5.94 ml, 43 mmol) in methanol (250 ml) was heated to 100° C. under 100 psi carbon monoxide for 12 hours. The reaction mixture was filtered through arbocel and the filtrate concentrated in vacuo and purified by flash column chromatography on silica gel eluting with dichloromethane:pentane (50:50 by volume) to afford the title compound as a yellow solid (3.76 g). 1H NMR (400 MHz, CDCl3) δ=7.92-7.90 (1H, m), 7.82 (1H, s), 7.35-7.34 (2H, m), 4.24 (1H, bs), 3.90 (3H, s), 3.05 (2H, s), 1.48 (9H, s), 1.26 (6H, s). LRMS (electrospray) m/z 208 [M+H−BOC]+

Provenance & Evidence