Hydrogen Peroxide → (S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methylmorpholin-3-one

HRID 16361

反応式

HRID 16361 の反応式
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[Si:15]([O:32][C@H:33]([CH3:53])[C@H:34]([N:44]1[CH2:49][C@H:48]([CH3:50])[O:47][C:46](=[O:51])[C:45]1=[O:52])[C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].OO.S([O-])(O)=O.[Na+]>C(OCC)(=O)C.C1COCC1>[Si:15]([O:32][C@H:33]([CH3:53])[C@H:34]([N:44]1[CH2:49][CH:48]([CH3:50])[O:47][C@H:46]([OH:51])[C:45]1=[O:52])[C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)([C:28]([CH3:29])([CH3:31])[CH3:30])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

8

反応物 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 23665763Sodium BisulfiteHCID 68718625(S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholine-2,3-dione

生成物 1

HCID 68717084(S)-4-[(1R,2R)-2-tert-butyl-diphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-2-hydroxy-6-methylmorpholin-3-one収率 97.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

In nitrogen atmosphere, a THF solution (0.25 mL) of 1.06 M lithium tri-sec-butyl borohydride was dropwise added at −20° C. to a THF solution (3 mL) of (S)-4-[(1R,2R)-2-tert-butyldiphenylsilanyloxy-1-(3,4,5-trifluorophenyl)propyl]-6-methylmorpholin-2,3-dione (95 mg). The resulting reaction solution was stirred at −20° C. for 30 min. To the reaction solution, a 5 N sodium hydroxide aqueous solution (0.03 mL) and a 30% hydrogen peroxide aqueous solution (0.07 mL) were added in this order. The resulting reaction solution was stirred under ice-cooling for 1 hr, and a sodium hydrogensulfite powder (20 mg) was added thereto. The resulting reaction solution was stirred at room temperature for 30 min, and then saturated saline and ethyl acetate were added thereto. The organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to give 93 mg of the title compound. The physical property values of this compound were as follows:

後処理

  1. customThe resulting reaction solution
  2. customThe resulting reaction solution
  3. stirringwas stirred under ice-
  4. temperaturecooling for 1 hr
  5. customThe resulting reaction solution
  6. stirringwas stirred at room temperature for 30 min
  7. customThe organic layer was separated
  8. washwashed with saturated saline
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-a3e7130beb1c4fa0bb5b1b71d585a005
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

関連ノート

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