Sodium hydride → HCID 67061784, Verbindung

HRID 910801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910801
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[NH:12][CH2:11][C@@H:10]2[O:27][CH:28]([C:39]2[CH:40]=[CH:41][C:42]3[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=3[CH:53]=2)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:5][CH:4]=1.[CH3:54][O:55][CH2:56][C@H:57]([CH3:60])[CH2:58][OH:59].[H-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C.O>[CH3:54][O:55][CH2:56][C@H:57]([CH3:60])[CH2:58][O:59][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][C@@H:13]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[NH:12][CH2:11][C@@H:10]2[O:27][CH:28]([C:39]2[CH:40]=[CH:41][C:42]3[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=3[CH:53]=2)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:5][CH:4]=1

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 56924404(2R)-3-Methoxy-2-methylpropan-1-olHCID 67061878HCID 67061878, Verbindung

Produkt 1

HCID 67061784HCID 67061784, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1.0 mmol of 6-[(3R,4R,6S)-4-(4-chloromethyl-phenyl)-1-(toluene-4-sulfonyl)-6-triisopropylsilanyloxymethyl-piperidin-3-yloxymethyl]-4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazine, 1.5 mmol of (R)-3-methoxy-2-methyl-propan-1-ol [911855-78-2] and 0.1 mmol of TBAI in 5 ml of DMF are added 1.65 mmol of NaH (55% in dispersion oil) at 0° C. The reaction mixture is allowed to warm to RT and stirred overnight, diluted with water, extracted with TBME and the organic phase is dried over Na2SO4. The organic phase is concentrated under reduced pressure and the residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a pale yellow oil. Rf=0.20 (EtOAc/heptane 1:2).

Aufarbeitung

  1. extractionextracted with TBME
  2. dry with materialthe organic phase is dried over Na2SO4
  3. concentrationThe organic phase is concentrated under reduced pressure
  4. customthe residue is purified by flash chromatography (SiO2 60 F)

Quellen und Nachweise

ORD-Eintrag
ord-148c59c4412a476eae5d580d264cff43
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022068B2

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