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

HRID 724679ノート

反応式

HRID 724679 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6850449aae0e4341a3ebf0f0fb88ad04
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

反応ノート

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