(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

HRID 884356노트

반응식

HRID 884356 반응식
[CH3:1][C:2]1([CH2:5][C@@:6]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:11][C:10](=[O:12])[N:9]([C@H:13]3[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]3)[CH2:8][CH2:7]2)[CH2:4][O:3]1>C1COCC1>[OH:3][C:2]([CH3:4])([CH3:1])[CH2:5][C@@:6]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:11][C:10](=[O:12])[N:9]([C@H:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]2)[CH2:8][CH2:7]1

참가 물질

3

반응물 1

HCID 58278664(3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate

생성물 1

HCID 58278660(S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate수율 19.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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).

후처리

  1. temperaturebefore being cooled to 0° C. again
  2. customThe mixture was quenched with water (10 mL), 1% aq HCl (25 mL)
  3. additiondiluted with EtOAc (120 mL)
  4. customAfter separation
  5. washthe organic layer was washed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified by chromatography on a 120 g silica gel column
  9. washeluted with a 50-100% EtOAc in hexanes gradient

출처 및 근거

ORD 기록
ord-acbada64fe85476e8f5be55ad9952f99
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242111B2

반응 노트

불러오는 중…