Sodium periodate → HCID 68499161, Verbindung

HRID 1712269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712269
[CH2:1]([O:4][CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:6]1)[CH:2]=C.I([O-])(=O)(=O)=[O:39].[Na+]>[Os](=O)(=O)(=O)=O.O1CCCC1.O>[OH:39][CH2:2][CH2:1][O:4][CH:5]1[CH:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[CH:15][CH:16]=2)[CH2:9][CH2:8][N:7]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:6]1

Komponenten

5

Edukt 2

HCID 23667635Sodium periodateHCID 68501888HCID 68501888, Verbindung

Produkt 1

HCID 68499161HCID 68499161, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

8.54 g of tert-butyl 3-allyloxy-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate are initially charged in a 3:1 tetrahydrofuran/water mixture (52 ml) with stirring at room temperature and admixed with 2.07 ml of osmium tetroxide (2.5% by wt. in tert-BuOH). Subsequently, 9.00 g of sodium periodate are added in portions. The reaction mixture is stirred further over 2 hours. The reaction mixture is concentrated by evaporation. The residue is suspended in a 1:1 dichloromethane/methanol mixture (150 ml), cooled to 5° C. and admixed with 3.96 g of sodium borohydride in portions. The reaction mixture is stirred at 5° C. for 1.5 hours and subsequently concentrated by evaporation. The residue is stirred in 200 ml of dichloromethane, filtered through glass fibre filter and washed with dichloromethane. The filtrate is washed with a 1:1 brine/water mixture, filtered through cotton wool, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.17 (1:1 EtOAc-heptane). Rt=5.22.

Aufarbeitung

  1. stirringThe reaction mixture is stirred further over 2 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. temperaturecooled to 5° C.
  4. stirringThe reaction mixture is stirred at 5° C. for 1.5 hours
  5. concentrationsubsequently concentrated by evaporation
  6. stirringThe residue is stirred in 200 ml of dichloromethane
  7. filtrationfiltered through glass
  8. filtrationfibre filter
  9. washwashed with dichloromethane
  10. washThe filtrate is washed with a 1:1 brine/water mixture
  11. filtrationfiltered through cotton wool
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-45919a46ca1840ca94cfe411ac34a726
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790715B2

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