Potassium Sodium Tartrate → HCID 69335514, compound

Participants

Reaction Conditions

Reaction Steps

To a flame dried, 3 neck rbf equipped with an addition funnel was added THF (20 mL) and titanium(IV) isopropoxide (2.6 mL, 8.8 mmol) and the flask immersed in a −78° C. bath. To this mixture was added isopropylmagnesium chloride (2M/diethyl ether, 8.8 mL, 17.6 mmol) dropwise and stirring continued at −78° C. for 15 minutes. To the reaction flask was then added the starting material (S)-(allyl-benzyl-amino)-phenyl-acetic acid methyl ester (JACS, 19, 30, 1997, 6984) (˜40% pure, 2.0 g, 2.7 mmol dropwise in THF (7 mL total) and the reaction was allowed to stir at −78° C. for 2.5 hours, warmed to −10° C., stirred for an additional 3 hours, allowed to warm to room temperature gradually and stirred for 16 hours. The reaction was poured carefully into a saturated Rochelle's Salt solution, solid sodium bicarbonate was added until the pH=8, EtOAc was added and the mixture allowed to stir for 1 hour. The phases were separated and the aqueous extracted with ETOAc, the combined organics were washed with brine and dried over calcium sulfate, filtered and concentrated. The crude product was purified on a Biotage flash 40 system eluted with a gradient of Hexanes to 12% ETOAc/Hexanes to give the title compound as an oil. (0.57 g, 32% yield).

Provenance & Evidence