Glutaraldehyde → HCID 86695044, compound

Participants

Reaction Steps

Compound 20 (120 mg, 0.47 mmol) and glutaraldehyde (46 mg, 0.23 mmol) was dissolved in 10 mL 1,2-dichloroethane and sodium triacetoxyborohydride (400 mg, 1.89 mmol) was added portionwise over 6 hrs and reaction was stirred overnight. The reaction was quenched with sat. sodium carbonate, extracted with EtOAc (2×25 mL), washed with water and then brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography provide the compound 22 (55 mg, 0.17 mmol, 36% yield). 1H NMR (CDCl3, 400 MHz) δ 7.23-7.28 (m, 2H), 6.68-6.94 (m, 7H), 4.10 (t, J=6.4 Hz, 2H), 3.72 (t, J=6.4 Hz, 2H), 3.50 (q, J=7.2 Hz, 2H), 3.05 (t, J=5.6 Hz, 4H), 1.72-1.78 (m, 4H), 1.54-1.60 (m, 2H), 1.22 (t, J=6.8 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C21H29N2O [M+H]+: 325.2280, found: 325.2227.

Provenance & Evidence