Diisopropylamine → Tert-butyl 2-pivaloylamino-beta-hydroxy-beta-phenyl-3-pyridinepropanoate

Participants

Reaction Conditions

Reaction Steps

In an atmosphere of argon, 1.69M n-butyl lithiumhexane solution (53 ml, 90.0 mmol) was added dropwise to an ether solution (150 ml) of diisopropylamine (9.61 g, 95.0 mmol) which was cooled at -78° C. After 15 minutes of stirring, an ether solution (20 ml) of tert-butyl acetate (10.5 g, 90.5 mmol) was slowly added dropwise. After 30 minutes of stirring, a tetrahydrofuran solution (30 ml) of 3-benzoyl-2-pivaloylaminopyridine (12.0 g, 42.6 mmol) was added dropwise. After 30 minutes of stirring, this was warmed up to room temperature and stirred for 5 hours. The reaction solution was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the resulting filtrate was concentrated under reduced pressure to give tert-butyl 2-pivaloylamino-β-hydroxy-β-phenyl-3-pyridinepropanoate (16.9 g, 100%).

Provenance & Evidence