tert-Butanol → HCID 86615516, Verbindung

HRID 1158768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158768
C=C1C[O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])C1.C[N+]1([O-])CC[O:29]CC1.S(=O)(O)[O-].[Na+].C(OCC)(=O)C.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:48][C:44]1([CH2:47][OH:29])[CH2:46][O:6][C@H:5]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=2[F:16])[C@@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:45]1

Komponenten

9

Edukt 5

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 86615515HCID 86615515, Verbindung

Produkt 1

HCID 86615516HCID 86615516, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl [(2R,3S)-5-methylene-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (203 mg, 0.59 μmmol) in tert-butyl alcohol (6 mL), acetone (3 mL) and water (1.5 mL) was added osmium tetroxide (0.113 mL of 2.5% solution in tert-butyl alcohol, 0.009 mmol). The resultant mixture was stirred at room temperature for 10 minutes and then treated with N-methylmorpholine N-oxide (92 mg, 0.79 mmol) and stirred for two days. After two days, the reaction mixture was treated with aqueous sodium bisulfite solution (5 mL, 2.0N) followed after 10 min by ethyl acetate. The organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and evaporated to yield tert-butyl [(2R,3S)-5-hydroxy-5-(hydroxymethyl)-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate which was used in the next step without further purification.

Aufarbeitung

  1. waitAfter two days
  2. washThe organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d7656aa1b6694acab43a784c4b84cd4d
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812027B2

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