Methanol → HCID 42636427, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ((1S,2R,3R,4R,6S)-4-(benzyloxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)-5-methylenecyclohexane-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene (34, 24 mg, 31.4 mmol) in anhydrous DCM (0.8 mL) in a vial at −78° C. under a nitrogen blanket was added BCl3 (1 M in DCM, 0.25 mL) drop-wise over 15 minutes. The resulting mixture was stirred at −78° C. for 30 minutes and gradually warmed to −20° C. The resulting mixture was stirred at −20° C. for another 30 minutes. At this time, LC-MS indicated that the reaction was complete. The solution was cooled to −78° C. and methanol (1 mL) was slowly added. The resulting solution was warmed to room temperature and concentrated under reduced pressure. The residue was dissolved in 0.5 mL of 1:1 DCM:MeOH and loaded on a preparative TLC plate, which was developed in 15:1 (DCM:MeOH) to obtain 9 mg (71%) of compound 35 as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.29-6.89 (m, 7H), 4.80 (s, 1H), 4.28 (s, 1H), 3.95 (m, 4H), 3.64 (m, 2H), 3.51(m, 3H), 3.22 (m, 1H), 2.58 (q, J=7.2 Hz, 2H), 2.25 (m, 1H), 1.18 (t, J=7.5 Hz, 3H). LC-ESI-MS m/z 425 (M+Na).

Provenance & Evidence