Water → HCID 178472378, Verbindung

HRID 928119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928119
[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH2:8])=[N:4][CH:3]=1.C[N+]1([O-])CC[O:24]CC1.C1COCC1.[OH2:33]>S([O-])([O-])(=O)=S.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)([OH:24])[CH2:8][OH:33])=[N:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 178437588HCID 178437588, Verbindung

Produkt 1

HCID 178472378HCID 178472378, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

Ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate (40 mg, 0.12 mmol), 4-methylmorpholine N-oxide (31 mg, 0.27 mmol), THF (0.8 ml), water (0.4 ml) and osmium tetroxide (0.22 ml, 0.028 mmol) were combined and the mixture was stirred at room temperature for 40 min. The mixture was then diluted with saturated sodium thiosulfate and extracted with EtOAc. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified on silica gel (EtOAc/hexane=1/1) to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1,2-dihydroxyethyl]cyclohexane-carboxylate. MS ESI calc'd. for C14H20BrNO4S [M+H]+ 378, 380. found 378, 380. 1H NMR (500 MHz, CDCl3) δ 7.55 (s, 1H), 4.15 (dd, J=5.7, 11.1, 1H), 4.07 (q, J=7.1, 2H), 3.74 (dd, J=7.0, 11.1, 1H), 2.61 (t, J=6.4, 1H), 2.20-2.10 (m, 1H), 2.05-1.84 (m, 3H), 1.85-1.70 (m, 1H), 1.60 (d, J=12.8, 1H), 1.46-1.13 (m, 5H), 1.13-1.05 (m, 1H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel (EtOAc/hexane=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-a13af991b984464b872839fe04b2b7ff
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290490B2

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