3-Methylpyridine-2-carboxaldehyde → 3{[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

Using General Procedure B: Reaction of 3-{[(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester in CH2Cl2 with 3-methyl-pyridine-2-carbaldehyde and NaBH(OAc)3 gave 3{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester as a sticky colorless oil. 1H NMR (CDCl3) δ 1.36 (s, 9H), 2.06 (s, 6H), 2.64-2.75 (m, 3H), 3.22-3.26 (m, 2H), 3.72 (s, 4H), 3.80 (t, 2H, J=7.5 Hz), 7.08-7.12 (m, 2H), 7.39 (d, 2H, J=6.0 Hz), 8.36 (d, 2H, J=3.0 Hz). Deprotection with TFA using General Procedure F gave azetidin-3-ylmethyl-bis-(3-methyl-pyridin-2-ylmethyl)-amine as a pale yellow sticky oil. 1H NMR (CDCl3) δ 1.85 (s, 1H), 2.10 (s, 6H), 2.73 (d, 2H, J=9.0 Hz), 2.94-2.99 (m, 1H), 3.09-3.12 (m, 2H), 3.49-3.54 (m, 2H), 3.70 (s, 4H), 7.08-7.12 (m, 2H), 7.39 (d, 2H, J=6.0 Hz), 8.37 (d, 2H, J=6.0 Hz).

Provenance & Evidence