3-amino-2-methylpropane-1,2-diol synthesis

Yield:-

Reaction Conditions:

with ammonia in methanol at 50 - 80; for 21 h;Sealed tube;

Steps:

A 250 mL steel bomb reaction vessel was loaded with (2-methyloxiran-2- yl)methyl 4-nitrobenzoate (both enantiomers available from Aldrich) (2.1 g, 8.85 mmol) in methanol (50 mL) to this was added ammonia (7 M in MeOH, 70 mL, 70 mmol). The vessel was sealed and heated to 80 °C for 3 hours and then stirred at 50 °C for 18 hours. The reaction was cooled to room temperature, concentrated and then taken up in 10 mL of MeOH. The suspension was cooled in a refrigerator for 1 hour and then filtered to remove residual solid. The filtrate was concentrated to provide the crude product as an amber oil (contains about 0.5 eq. of the 4-nitrobenzamide as a byproduct). Yield not determined, material used as is. (NMR omits impurity peaks for clarity) ‘H NMR (400MHz, CHLOROFORM-d)? 3.64(d,J11.OHz, 1H), 3.49 (dd,J11.0, 1.0 Hz, 1H), 2.88-2.75 (m, 2H), 1.10(s, 3H). Not visible by UV or MS.

References:

WO2017/87590,2017,A1 Location in patent:Page/Page column 101; 102