2-Methoxypropene → Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoate

Participants

Reaction Conditions

Reaction Steps

120 ml of isopropenyl methyl ether are added to a solution of 159.5 g of methyl 4(S)-tert-butoxycarbonylamino-5-hydroxyvalerate and 3 g of p-toluenesulfonic acid hydrate in 500 ml of methylene chloride at 0° C. The reaction mixture is stirred at 0° C. for 2 h and at room temperature for 3 h. The reaction solution is washed with 100 ml of saturated sodium bicarbonate solution and evaporated. The title compound is obtained by FC (800 g of silica gel, mobile phase E): [α]D =+20.5 (c=0.8 in CHCl3); Rf (D)=0.24; MS: (M)+ =287.

Provenance & Evidence