Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoate → (S)-tert-butyl 4-(2-(1-hydroxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

The (S)-tert-butyl 4-(3-methoxy-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (1.02 g, 3.55 mmol, 1.0 equiv) was dissolved in 50 mL of THF and cooled to −10° C. A 1.0 M solution of BrMg(CH2)4MgBr (7.1 mL, 2.0 equiv) was added and the mixture stirred for 2 h. After this time a second portion of BrMg(CH2)4MgBr was added and the mixture stirred for 1 h. The mixture was quenched by addition of saturated NH4Cl and the mixture transferred to a separatory funnel, and the organic layer was washed with brine, then dried over Na2SO4, filtered, and evaporated to provide crude (S)-tert-butyl 4-(2-(1-hydroxycyclopentyl)ethyl)-2,2-dimethyloxazolidine-3-carboxylate.

Provenance & Evidence