Sodium triacetoxyborohydride → 4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-phenyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

Using General Procedure B: Reaction of the amine from above and 3,5-dimethyl-2-pyridinecarboxaldehyde in CH2Cl2 with NaBH(OAc)3 gave 4-[(3,5-dimethyl-pyridin-2-ylmethyl)-(3-phenyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester. 1H NMR (CDCl3) δ 1.20 (m, 3H), 1.40 (s, 9H), 1.84 (s, 3H), 2.20 (s, 3H), 2.34 (m, 2H), 2.75 (m, 4H), 3.69 (s, 2H), 3.79 (s, 2H), 7.04 (s, 1H), 7.22 (m, 6H), 7.46 (dd, 1H, J=7.27, 1.7 Hz), 8.01 (s, 1H), 8.49 (dd, 1H, J=4.8, 1.7 Hz) ppm. Deprotection with CH2Cl2/TFA using General Procedure F gave (3,5-dimethyl-pyridin-2-ylmethyl)-(3-phenyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine. 1H NMR (CDCl3) δ 1.72 (m, 2H), 1.92 (m, 2H), 2.34 (s, 3H), 2.44 (s, 3H), 2.70 (m, 3H), 3.25 (m, 2H), 4.16 (m, 4H), 7.28 (m, 2H), 7.45 (m, 3H), 7.58 (q, 1H, J=4.38 Hz), 7.86 (m, 2H), 8.49 (s, 1H), 8.80 (d, 1H, J=3.38 Hz) ppm.

Provenance & Evidence