Sodium triacetoxyborohydride → HCID 69482688, compound

Participants

Reaction Steps

A solution of ethyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate (1.78 g, 6.5 mmol) and phenylmethyl methyl(2-oxoethyl)carbamate (2.58 g, 12.4 mmol) under nitrogen in glacial acetic acid (300 mL) was treated with sodium triacetoxyborohydride (2.56 g, 12.1 mmol) at ambient temperature overnight. Concentrated the reaction in vacuo then redissolved in glacial acetic acid (100 mL) and treated with another 1 g of sodium triacetoxyborohydride at ambient temperature for 2 h. The reaction was evaporated in vacuo and the residue was chromatographed on silica gel eluting with 98:2-95:5 CH2Cl2:EtOAc to provide a clear viscous oil. The oil was dissolved in CH2Cl2, washed with saturated K2CO3, water, and brine, dried over Na2SO4, filtered and evaporated in vacuo to afford the product as a yellow viscuos oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.27 (t, J=7.09 Hz, 3 H), 2.87 (d, J=5.90 Hz, 3 H), 3.34-3.51 (m, 4 H), 3.89 (d, J=20.22 Hz, 2 H), 4.24 (q, J=7.16 Hz, 2 H), 5.02 (d, J=23.16 Hz, 2 H), 7.09 (t, J=8.84 Hz, 2 H), 7.18-7.39 (m, 7 H), 7.66 (d, J=16.00 Hz, 1 H), 7.77 (s, 1 H); ES+ MS: 466 (M+H+).

Provenance & Evidence