Tetrahydrofuran → 3-Hydroxymethyl-2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-3-methanol 1,1-dioxide
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:15]([C:16](OCC)=[O:17])=[CH:14][C:13]3[CH:21]=[CH:22][S:23][C:12]=3[S:11]2(=[O:25])=[O:24])=[CH:5][CH:4]=1.CC(C[AlH]CC(C)C)C.C1C[O:38][CH2:37]C1>>[OH:38][CH2:37][C:15]1([CH2:16][OH:17])[CH2:14][C:13]2[CH:21]=[CH:22][S:23][C:12]=2[S:11](=[O:24])(=[O:25])[N:10]1[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1Komponenten
4
Versuchsvorschrift
To a solution of the product from Step B (1.80 g, 4.75 mmol) in anhydrous THF (40 mL) at ambient temperature was added DIBAL (1.0M, 11.87 mL, 11.87 mmol) and the mixture was stirred for 1 h. Additional DIBAL (1M, 15 mL,15 mmol) was added (TLC showed starting material remained) and the reaction mixture was stirred for 20 h, cooled (ice bath) and the reaction was quenched by the slow addition of 1N HCl (100 mL). THF was evaporated and the aqueous mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4), filtered and evaporated to give an oil (1.60 g) which was used in the next step without further purification.
Aufarbeitung
- stirringthe reaction mixture was stirred for 20 h
- temperaturecooled (ice bath)
- customthe reaction was quenched by the slow addition of 1N HCl (100 mL)
- customTHF was evaporated
- extractionthe aqueous mixture was extracted with ethyl acetate (2×100 mL)
- dry with materialThe combined extracts were dried (MgSO4)
- filtrationfiltered
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-7498f9ebe14d4d3f8bcc298920919814
- Quelldatensatz
- uspto-grants-1996_07
- Patentnummer
- US05538966
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