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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 932243
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Reaktionsgleichung

Reaktionsgleichung von HRID 932243
[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]
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Komponenten

4

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-Dichloroethane
Lösungsmittel

Versuchsvorschrift

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 3d. 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-104095726e8b4804a22c21ee5b0fd102
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296736B2

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