HCID 59201637, compound → HCID 59201552, compound

Participants

Reaction Steps

The (S)-tert-butyl 4-((R)-4-(1-hydroxycyclopropyl)-2-(tosyloxymethyl)butyl)-2,2-dimethyloxazolidine-3-carboxylate was dissolved in 30 mL of THF and MeMgBr (7.0 mL of a 3.0 M solution, 2.0 equiv) was added and the mixture heated to reflux for 56 hr. After cooling to ambient the mixture was quenched by addition of water and the mixture transferred to a separatory funnel. The layers were separated and the organic layer were washed with brine, dried over Na2SO4, filtered and evaporated. The pyran derivative was purified by flash chromatography on silica (40 g) eluting with 0-29% EtOAc in hexanes. This afforded 1.05 g (91% yield) of (S)-tert-butyl 4-(((R)-4-oxaspiro[2.5]oct-6-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate. MS ESI +ve m/z 348 (M+Na).

Provenance & Evidence