Methanol → HCID 11518161, compound

Participants

Reaction Steps

To a suspension of 3I (80 mg, 0.17 mmol) in THF (1 mL) at RT under argon was added borane-tetrahydrofuran complex (0.85 mL, 0.85 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 reaction was stirred at RT for overnight. The solvent was concentrated. The resultant residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3 (20 mL). The layers were separated. The aqueous layer was extracted with CH2Cl2 (20 mL×3). The combined organics were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The resultant residue was purified by silica gel (10 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as a white foam (71 mg, 88%). LC/MS (method A): retention time=2.69 min, (M+H)+=456. 1H-NMR (CDCl3, 400 MHz): δ8.00 (s, 1H), 7.75-7.85 (m, 4H), 7.47-7.55 (m, 1H), 7.10-7.48 (m, 11H), 5.44 (d, J=8.2 Hz, 1H), 4.30 (dd, J1=90 Hz, J2=16.4 Hz, 2H), 3.80-3.90 (m, 1H), 3.35-3.45 (m, 1H), 3.10 (dd, J1=4.9 Hz, J2=1.8 Hz, 1H), 2.93 (dd, J1=16.7 Hz, J2=4.5Hz, 1H), 2.65 (dd, J1=4.9 Hz, J2=1.8 Hz, 1H).

Provenance & Evidence