Triphenylphosphine → HCID 118093072, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 17D (556 mg, 1.852 mmol), (R)-1-methoxypropan-2-ol (367 mg, 4.07 mmol), triphenylphosphine (1068 mg, 4.07 mmol) in THF (5 mL) was added DIAD (0.81 mL, 4.07 mmol). The reaction mixture was stirred at 0° C. for 30 min, and at rt for 16 h. The mixture was concentrated and purified by flash chromatography. The desired fractions were combined and concentrated. The residue was dissolved in MeOH (30 mL) and THF (10 mL). Zinc (dust) (3.47 g, 53.1 mmol) and ammonium chloride (5.68 g, 106 mmol) were added. The resulting solution was stirred at rt for 2 h. MeOH was removed under reduced pressure. Na2CO3 (aq, 100 mL) and EtOAc (150 mL) was added, and the suspension was stirred vigorously for 10 min. The mixture was filtered through a glass frit, solid residue was washed with EtOAc (3×150 mL). Combined EtOAc fractions were washed with std. Na2CO3 (aq, 2×50 mL), water (2×50 mL), brine (1×50 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was dissolved in EtOAc (10 mL), treated with HCl (4M, 8 mL) for 2 h at rt. The solvent was removed under reduced pressure to yield 37A (520 mg, 1.650 mmol, 89% yield) as a yellow solid. MS (ESI) m/z: 244.3 (M+H)+.

Provenance & Evidence