Methanol → HCID 11691039, compound

Participants

Reaction Steps

To a suspension of 2C (45 mg, 0.096 mmol) in THF (1 mL) at RT under argon was added borane-tetrahydrofuran complex (1 M solution in THF, 0.48 mL, 0.48 mmol) dropwise. After the addition, the reaction became a clear solution. The reaction was allowed to stir at RT under argon for 1 h. After this time, no starting material was detected by LC-MS. MeOH (1 mL) was added carefully to the reaction and the mixture was stirred at RT for 60 min, then concentrated under reduced pressure. The resulting residue was partitioned between CH2Cl2 (30 mL) and saturated aqueous NaHCO3. The layers were separated. The aqueous layer was extracted with CH2Cl2 (20 mL). The combined organic layer were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The resultant residue was dissolved in boiling CH3CN (2 μL) and EtOAc (2 mL), and then hexane (10 mL) was added. After cooling to RT. White precipitates foamed. The product was collected by filtration and washed with hexane to give the title compound as a white solid (33 mg, 76%). HPLC (method B): 99% at 5.62 min. MS (ES): m/z 456 [M+H]+. 1H NMR (DMSO6, 400 MHz): δ 8.13 (d, J=6.2 Hz, 1H), 7.92-7.96 (m, 4H), 7.64-7.76 (m, 3H), 7.59 (d, J=8.6 Hz, 1H), 7.29-7.46 (m, 4H), 7.28-7.34 (m, 4H), 7.00 (d, J=8.6 Hz, 1H), 4.54 (dd, J1=48.9 Hz, J2=16.5 Hz, 2H), 3.40-3.45 (m, 1H), 3.36-3.40(m, 1H), 3.25-3.29 (m, 1H), 2.90-3.01(m, 2H).

Provenance & Evidence