Methanol → HCID 67389224, compound

Participants

Reaction Steps

The product from Step A (320 mg, 0.603 mmol) was partially dissolved in THF (20 mL) at room temperature. Borane-methyl sulfide complex (3.62 mL, 3.62 mmol) was added. The mixture was stirred at room temperature for 1 h, and then refluxed overnight. Borane-methyl sulfide complex (1.206 mL, 1.206 mmol) was added to the solution and the mixture was stirred at room temperature for 0.5 h, and then heated to (65-67° C.) for 6 h. Methanol (4 mL) was added with caution and the mixture was concentrated under reduced pressure. The residue was dissolved in n-PrOH (45 mL) and the solution was refluxed for overnight. The residue was purified by column chromatography on silica gel Biotage 25M™, eluting with EtOAc/CH2Cl2 (gradient from 0% to 60%) to give the desired product which was treated with 1:1 TFA/CH2Cl2 for 1 h. The residue was purified by preparative TLC on silica gel, eluting with CH2Cl2/MeOH/aqueous NH3 (90/9/1) to give the title compound. LC-MS: 416.91 (M+1).

Provenance & Evidence