反应详情

To a solution of 3-(4-amino-2-fluorophenyl)-3-hydroxy-1-(1,1-diphenylmethyl)azetidine (Example 81, Step 1, 5.10 g, 14.7 mmol) in acetone (75 mL) was added a solution of sodium bicarbonate (2.52 g, 30.0 mmol) in water (40 mL) to give a creamy suspension. Benzyl chloroformate (2.57 g, 15.1 mmol) was added and stirring continued overnight. The suspension was filtered and the acetone evaporated. The residue was partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer was washed with brine (50 mL), dried over magnesium sulfate, filtered and evaporated to leave an amber foam. Chromatography over silica gel (150 g, 40-60 μM) eluting with 1-2% methanol-methylene chloride gave the title compound as a cream foam. HRMS: meas. 483.2087, theory 483.2084.

1. customto give a creamy suspension
2. filtrationThe suspension was filtered
3. customthe acetone evaporated
4. customThe residue was partitioned between ethyl acetate (200 mL) and water (50 mL)
5. washThe organic layer was washed with brine (50 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customto leave an amber foam
10. washChromatography over silica gel (150 g, 40-60 μM) eluting with 1-2% methanol-methylene chloride