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

HRID 724679Notes

Reaction equation

HRID 724679 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6850449aae0e4341a3ebf0f0fb88ad04
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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