Sodium borohydride → 3-Diphenylmethyl-1,2,3,6-tetrahydropyridin-1-yl acetic acid ethyl ester

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Reaction Steps

To an ice cooled solution of 0.206 g (0.5 mmol) 1-ethoxycarbonylmethyl-3-diphenylmethylpyridinium bromide (from step 1) was added 0.034 g (0.92 mmol) sodium borohydride in small portions with stirring over one hour. The solvent was evaporated, the residue dissolved in diethyl ether, washed with water and dried with magnesium sulphate. After evaporation of the solvent, the residue was chromatographed on silica gel column with 30% ethyl acetate in hexanes to give 0.107 g (64%) 3-diphenylmethyl-1,2,3,6-tetrahydropyridin-1-yl acetic acid ethyl ester (compound C1) as a pale yellow oil. NMR spectra showed: 1H NMR (CDCl3, 300 MHz) δ 7.40-7.10 (m, 10 H), 5.22 (br. s,1 H), 4.61 (s, 1 H), 4.12 (q, 2 H), 3.25 (s, 2 H), 3.03 (s, 2 H), 2.68 (t, 2 H), 2.22 (br. s, 2 H), 1.19 (t, 3 H); 13C NMR (CDCl3 75 MHz) δ 170.24, 141.86, 137.89, 129.11, 128.10, 126.19, 123.24, 60.31, 58.79, 56.24, 55.13, 49.51, 25.64, 14.05. El-MS: 335 (10, M+, C22H25NO2), 262 (50).

Provenance & Evidence