반응 #971538

반응 방정식

(3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate

→

(S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate

수율 19.1%

용매

THF

반응 조건

후처리

1. 1
   온도before being cooled to 0° C. again
2. 2
   기타The mixture was quenched with water (10 mL), 1% aq HCl (25 mL)
3. 3
   workup.ADDITIONdiluted with EtOAc (120 mL)
4. 4
   기타After separation
5. 5
   세척the organic layer was washed with brine (20 mL)
6. 6
   건조dried over Na2SO4
7. 7
   여과After filtration and concentration
8. 8
   기타the residue was purified by chromatography on a 120 g silica gel column
9. 9
   세척eluted with a 50-100% EtOAc in hexanes gradient

실험 절차

A solution of (3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate (2.87 g, 6.67 mmol) in dry THF (50 mL) was cooled to 0° C. After 20 min, the mixture was allowed to warm up to rt slowly. The mixture was stirred 2 h at rt, before being cooled to 0° C. again. The mixture was quenched with water (10 mL), 1% aq HCl (25 mL), diluted with EtOAc (120 mL). After separation, the organic layer was washed with brine (20 mL), dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 120 g silica gel column, eluted with a 50-100% EtOAc in hexanes gradient, to afford (S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate (0.55 g, 19% yield). LC-MS Method 1 tR=1.64 min., m/z 455 (M+Na).

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