Benzyl Alcohol → HCID 90405970, compound

Participants

Reaction Conditions

Reaction Steps

To the title compound of step A (10 g, 41 mmol) in PhCH3 (60 mL) was added DIPEA (7.4 mL, 43 mmol) and the mixture heated at 50° C. for 1 h. Then DPPA (8.9 mL, 41 mmol) in PhCH3 was added dropwise and the mixture heated at 75° C. for 2 h and BnOH (4.5 mL, 43 mmol) and the mixture stirred at 80° C. for 20 h. The reaction was allowed to cool to rt, diluted with saturated NaHCO3 (aq) and extracted with PhCH3. The combined organics were dried (MgSO4). Purification via silica gel chromatography (0-20% EtOAc in hexanes) gave the title compound (2.6 g, 18%). MS (ESI) mass calcd. for C19H28N2O4, 348.2; m/z found 249.2 [M−100]+, 293.2 [M−55]+. 1H NMR (400 MHz, CDCl3) 7.39-7.30 (m, 5H), 5.24-5.00 (m, 3H), 4.35-4.22 (m, 1H), 4.01-3.85 (m, 1H), 3.74-3.51 (m, 1H), 2.89-2.71 (m, 1H), 1.87-1.30 (m, 13H), 1.19 (d, J=7.0 Hz, 3H).

Provenance & Evidence