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

HRID 724679노트

반응식

HRID 724679 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6850449aae0e4341a3ebf0f0fb88ad04
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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