Sodium triacetoxyborohydride → HCID 69482270, compound

Participants

Reaction Steps

A mixture of ethyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate (1.21 g, 4.10 mmol) and phenylmethyl methyl(3-oxopropyl)carbamate (1.63 g, 7.39 mmol) in glacial acetic acid (15 mL) was treated with sodium trisacetoxyborohydride (1.74 g, 8.21 mmol) and stirred under nitrogen at ambient temperature. After approximately 1 hour, additional sodium triacetoxyborohydride (1.00 g, 4.72 mmol) was added. After an additional 3-4 hours, additional phenylmethyl methyl(3-oxopropyl)carbamate (1.00 g, 4.52 mmol) and sodium triacetoxyborohydride (1.00 g, 4.72 mmol) was added. The reaction mixture was evaporated in vacuo and the residue was dissolved in CH2Cl2 and treated with 2N KOH. After separating the layers, the aqueous phase was back-extracted with CH2Cl2 and the combined organic layers were washed with water, dried over MgSO4, filtered, evaporated in vacuo and purified on silica eluting with 3% MeOH in CH2Cl2 to provide the product as an oil: 1H NMR (CDCl3) δ 7.88 (1H, s), 7.77 (1H, s), 7.26-7.37 (5H, m), 7.11 (2H, b), 6.97 (2H, t, J=8.8), 6.74 (1H, d, J=31 Hz), 5.12 (2H, s), 4.42 (2H, q, J=7 Hz), 3.90 (2H, s), 3.41 (2H, t, J=7), 3.06-3.20 (2H, m), 2.92 (3H, s), 1.86 (2H, b), 1.42 (3H, t, J=7 Hz); ES+ MS: 480 (M+H+).

Provenance & Evidence