2-Pyridinecarboxaldehyde → Tert-butyl 2-((8-(tert-butoxycarbonylamino)octyl)(pyridin-2-ylmethyl)amino)acetate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 8-aminooctylcarbamate (1.61 g, 6.588 mmol), 2-pyridinecarboxaldehyde (0.63 mL, 6.588 mmol) and AcOH (0.10 mL) in DCE (30 mL) was heated at 75° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated sequentially with NaBH(OAc)3 (3.708 g, 17.5 mmol) and tert-butyl glyoxalate (1.53 g)1. The reaction mixture was stirred at room temperature overnight and quenched with water. The reaction mixture was then extracted with DCM and the organic layers was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford tert-butyl 2-((8-(tert-butoxycarbonylamino)octyl)(pyridin-2-ylmethyl)amino)acetate (1.71 g, 58%) as a yellow oil. 1H NMR (400 MHz, CD3Cl3) δ 8.52 (d, J=4.8 Hz, 1H), 7.65 (td, J=7.8, 1.6 Hz, 1H), 7.56 (d, J=7.6, 1H), 7.18-7.12 (m, 1H), 4.50 (s, 1H), 3.90 (s, 2H), 3.28 (s, 2H), 3.07 (q, J=6.3 Hz, 2H), 2.61 (t, J=7.6 Hz, 2H), 1.50-1.24 (m, 30H); ESMS m/z: 450.4 (M+H)+.

Provenance & Evidence