Sodium triacetoxyborohydride → {2-[(5,6,7,8-Tetrahydro-quinolin-8-ylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

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Reaction Steps

Using General Procedure B: Reaction of 5,6,7,8-tetrahydro-quinolin-8-ylamine in CH2Cl2 with (2-formyl-pyridin-3-yl)-carbamic acid tert-butyl ester and NaBH(OAc)3 gave {2-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester as a yellow oil. 1H NMR (CDCl3) δ 1.51 (s, 9H), 1.85-1.94 (m, 2H), 1.98-2.08 (m, 2H), 2.78-2.84 (m, 2H), 3.82-3.86 (m, 1H), 4.19 (s, 2H), 7.11-7.19 (m, 2H), 7.42 (d, 1H, J=7.1 Hz), 8.15-8.17 (m, 1H), 8.28 (d, 1H, J=8.0 Hz), 8.44 (d, 1H, J=3.0 Hz), 10.17 (s, 1H).

Provenance & Evidence