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Sodium Bicarbonate → (3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-3-methylpiperidin-2-one

HRID 1048557
ノート
印刷プレビュー

反応式

HRID 1048557 の反応式
[O-]S(C(F)(F)F)(=O)=O.[CH2:9]([C@@:12]1([CH3:39])[CH2:17][C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C@@H:15]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N+:14]2[C@@H:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:33][O:34][C:13]1=2)[CH:10]=[CH2:11].C([O-])(O)=[O:41].[Na+]>ClCCCl>[CH2:9]([C@@:12]1([CH3:39])[CH2:17][C@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[C@@H:15]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[N:14]([C@@H:32]([C:35]([CH3:37])([CH3:38])[CH3:36])[CH2:33][OH:41])[C:13]1=[O:34])[CH:10]=[CH2:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 86660745(3S,5S,6R,8S)-8-Allyl-3-(tert-butyl)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium triflate

生成物 1

HCID 58574025(3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-3-methylpiperidin-2-one

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
50 °C

実験手順

To a solution of (3S,5S,6R,8S)-8-allyl-3-(tert-butyl)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium trifluoromethanesulfonate (290 mg, 0.478 mmol; Example 363, Step B) in 1,2-dichloroethane (4.78 mL) was added 5 mL of sat. aq. NaHCO3 solution. The reaction mixture was heated to 50° C. for 3 d. The reaction mixture was poured into a separatory funnel and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and the filtrate was concentrated. Purification by column chromatography using 25-35% ethyl acetate in hexanes on a 4 g silica gel column afforded the title compound.

後処理

  1. additionThe reaction mixture was poured into a separatory funnel
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with sat. aq. NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customPurification by column chromatography

出典と根拠

ORDレコード
ord-b2905d812a4a4506813c22e53d3be56c
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569341B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート