(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 884356ノート

反応式

HRID 884356 の反応式
[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

参加物

3

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-acbada64fe85476e8f5be55ad9952f99
出典データセット
uspto-grants-2012_08
特許番号
US08242111B2

反応ノート

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