反应详情

To a solution of borane-trimethylamine complex (1.35 mL of a 1 M solution in tetrahydrofuran) in tetrahydrofuran (3 mL) stirring at 0° C., a solution of 4-(tert-butyl)-2-(1-Boc-piperidine-4-yloxy)benzoic acid (0.51 g, 1.35 mmol) in tetrahydrofuran (7 mL) was added slowly via cannula. After the addition was complete the reaction mixture was stirred at room temperature for 4 h, then an additional amount of borane-trimethylamine complex was added (1.35 mL of a 1 M solution in tetrahydrofuran). The reaction mixture was stirred at room temperature for another 2 h. After quenching with ice, the mixture was partitioned between brine and dichloromethane. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to a residue (0.42 g, 86%) which was identified as the title compound and used directly in the next step without further purification.

1. additionAfter the addition
2. stirringThe reaction mixture was stirred at room temperature for another 2 h
3. customAfter quenching with ice
4. customthe mixture was partitioned between brine and dichloromethane
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (3×)
7. dry with materialThe combined organic layers were dried with magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo to a residue (0.42 g, 86%) which
10. customused directly in the next step without further purification