Ammonium Hydroxide → Ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(methyl)phosphinate

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Reaction Steps

To a solution of ethyl 3-[ethoxy(methyl)phosphoryl]-2-fluorobutanoate (3.0 g, 12.4 mmol) in ethanol (15 mL) was added concentrated ammonium hydroxide (14.8 M, 1.3 mL, 19 mmol). The solution was stirred for 24 h at room temperature and then at 50° C. for 2 hours. Another portion of concentrated ammonium hydroxide (14.8 M, 0.5 mL, 7 mmol) was added and the mixture was stirred at room temperature for three days and then evaporated to give 2.4 g (91%) of a diastereomeric mixture of ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(methyl)phosphinate as a clear oil. 1H NMR (400 MHz, CDCl3) δ5.9-6.7 (m, 2H), 4.9-5.6 (m, 1H), 4.0-4.2 (m, 2H), 2.5-2.8 (m, 1H), 1.2-1.6 (m, 9H).

Provenance & Evidence