Triethylamine → 3-Methyl-1-(5-nitro-pyridin-2-ylmethyl)azetidin-3-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 52 (0.5 g, 2.2 mmol) in MeOH (25 mL) was added Ambersep-900 OH resin (50 g) filtered to separate the resin and concentrated to obtain the free base. The free base was dissolved in MeOH-THF (10 mL, 1:1) and cooled to 0° C. 3-methyl-azetidin-3-ol (0.53 g, 4.3 mmol) and triethylamine (0.7 mL, 4.3 mmol) were added and the reaction mixture warmed to rt and stirred for 16 h. The reaction mixture was concentrated and the crude compound was purified by silica gel column chromatography (100-200 mesh), eluting with 3% MeOH/CHCl3 to give the desired compound (0.35 g, 48%, over two steps) as a pale yellow liquid. Rf: 0.3 (10% MeOH/DCM); (m/z): 224 [MH]+; 1H NMR (400 MHz, DMSO-d6): δ 9.27 (1H, d, J=2.4 Hz), 8.56 (1H, dd, J=8.8, 2.8 Hz), 7.64 (1H, d, J=8.8 Hz), 5.22 (1H, s), 3.85 (2H, s), 3.36-3.26 (2H, m), 3.02-3.00 (2H, m), 1.38 (3H, s).

Provenance & Evidence