Hydrochloric Acid → HCID 25073814, compound

Participants

Reaction Steps

The product from Example 79B (20.4 mg, 0.061 mmol) was treated with 0.091 M formaldehyde in CH3CN (0.80 mL, 0.073 mmol), diluted with CH3CN (2.24 mL), treated with NaCNBH3 (7.6 mg, 0.12 mmol), treated dropwise with a solution of 0.48 M HCl in CH3CN to keep the reaction at approximately a pH of 6 and then stirred for 1 hour. The mixture was directly purified by chromatography on silica gel (2, 3.5 and 5% (9:1 MeOH:saturated aqueous NH4OH) in CH2Cl2) to provide 9.6 mg of the title compound. The 0.48 M HCl in CH3CN was prepared by diluting 1 mL of concentrated HCl to 25 mL with CH3CN. The 0.091 M formaldehyde solution was prepared by diluting 37% aqueous formaldehyde with CH3CN. 1H NMR (CDCl3) δ 1.63-1.76 (m, 1H), 1.76-1.89 (m, 1H), 2.10-2.21 (m, 2H), 2.21-2.36 (m, 3H), 2.28 (s, 3H), 2.37-2.55 (m, 5H), 2.65 (t, J=6.78 Hz, 2H), 3.55 (dd, J=10.85, 5.43 Hz, 1H), 3.62-3.75 (m, 3H), 4.77 (s, 2H), 7.18-7.23 (m, 1H), 7.29-7.39 (m, 2H), 7.75-7.79 (m, 1H); MS (M+H)+ m/z 350.

Provenance & Evidence