Methanol → Tert-butyl 3-(4-amino-2-methoxyphenoxy)azetidine-1-carboxylate

Participants

Reaction Steps

Dissolve 3-(2-methoxy-4-nitro-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (210 g, 639 mmol) in THF (630 mL) and transfer with MeOH (1680 mL) to a stainless steel tank containing 10% palladium on carbon pre-wet with toluene. Hydrogenate the mixture on a Parr shaker for 2.5 h. Remove the catalyst by filtration through diatomaceous earth and rinse the solids with MeOH. Concentrate the filtrate in vacuo, and then co-evaporate the residue three times with heptane (500 mL each time) to obtain 190 g (99%) of the title compound as a tan solid which is used immediately in the next reaction. 1H NMR (300 MHz, CDCl3) δ: 6.48 (d, 1H, J=8.5), 6.30 (d, 1H, J=2.6), 6.17 (dd, 1H, J=2.4, 8.5), 4.77 (m, 1H), 4.19 (m, 2H), 4.04 (m, 2H), 3.81 (s, 3H), 3.59 (br s, 2H), 1.42 (s, 9H).

Provenance & Evidence