Potassium trimethylsilanolate → (1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2118324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118324
[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][C@@H:28]([C:30]4[CH:41]=[CH:40][C:33]5[O:34][C:35]([CH3:39])([CH3:38])[O:36][CH2:37][C:32]=5[CH:31]=4)[O:27]C3=O)[CH:11]=[CH:12][CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>O1CCCC1>[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:29][C@@H:28]([C:30]3[CH:41]=[CH:40][C:33]4[O:34][C:35]([CH3:38])([CH3:39])[O:36][CH2:37][C:32]=4[CH:31]=3)[OH:27])[CH:11]=[CH:12][CH:13]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 2

HCID 23668039Potassium trimethylsilanolateHCID 69119380(5R)-3-(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Produkt 1

HCID 69119885(1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanolAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred mixture of (5R)-3-(6-{4-[3-(cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.14 g) and potassium trimethyl silanolate (0.45 g) in tetrahydrofuran (10 ml) was heated to reflux for 2 h. The mixture was poured into phoshate buffer solution (pH 5, 50 ml) and extracted into ethyl acetate. The extracts were washed with water, dried (Na2SO4) and evaporated. The residual oil was purified on a biotage cartridge (8 g) using dichloromethane-ethanol-0.88 ammonia (100:8:1) as eluent. The appropriate fractions were evaporated to give the title compound (0.11 g) LCMS RT=2.89 min.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. extractionextracted into ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residual oil was purified on a biotage cartridge (8 g)
  8. customThe appropriate fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-dd5b4e1fab2245d59fce3eec26043ae6
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442839B2

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