Lithium borohydride → 5-[2-Bromo-4-(hydroxymethyl)phenyl]isothiazolidin-3-one 1,1-dioxide

HRID 724679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724679
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]1[S:16](=[O:18])(=[O:17])[NH:15][C:14](=[O:19])[CH2:13]1)[C:5](OC)=[O:6].[BH4-].[Li+]>O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][C:11]=1[CH:12]1[S:16](=[O:17])(=[O:18])[NH:15][C:14](=[O:19])[CH2:13]1

Komponenten

5

Edukt 2

HCID 4148881Lithium borohydrideHCID 57354419Methyl 3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzoate

Produkt 1

HCID 218791345-[2-Bromo-4-(hydroxymethyl)phenyl]isothiazolidin-3-one 1,1-dioxideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 3-bromo-4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)benzoate (77.0 mg, 0.221 mmol) in tetrahydrofuran (6 mL) was added 2 M lithium tetrahydroborate in tetrahydrofuran (332 μL) at room temperature. The resulting solution was stirred at room temperature overnight. The reaction solution was diluted with methanol, and stirred for 0.5 h. The crude material was purified by preparative LCMS to give a white solid (65 mg, 92%). 1H NMR (400 MHz, CD3OD): δ 7.57 (s, 1H), 7.46 (m, 2H), 5.30 (dd, J=9.0, 5.9 Hz, 1H), 4.49 (s, 2H), 3.26 (m, 1H), 2.97 (dd, J=17.2, 5.7 Hz, 1H). LCMS found for C10H10BrNO4SNa (M+Na)+: m/z=342, 344.

Aufarbeitung

  1. stirringstirred for 0.5 h
  2. customThe crude material was purified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-6850449aae0e4341a3ebf0f0fb88ad04
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141596B2

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