Lithium borohydride → 2-Tert-butyl-5-(4-hydroxymethyl-phenyl)-1,1-dioxo-1lambda6-isothiazolidin-3-one

HRID 724625Notes

Reaction equation

HRID 724625 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=2)[S:6]1(=[O:20])=[O:19])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=2)[S:6]1(=[O:20])=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 587465472-Tert-butyl-5-(4-hydroxymethyl-phenyl)-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

Product 1

HCID 587465972-Tert-butyl-5-(4-hydroxymethyl-phenyl)-1,1-dioxo-1lambda6-isothiazolidin-3-oneYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 20-A of Example 1.20 (420 mg, 1.4 mmol) in tetrahydrofuran (8.4 mL) at 0° C. was treated with lithium tetrahydroborate (0.71 mL, 1.4 mmol, 2 M in tetrahydrofuran). The reaction mixture was stirred at 0° C. for 30 min and quenched with acetic acid (1 mL). The reaction mixture was concentrated and purified by preparative LCMS to yield 4.15-C (359 mg, 85%). LCMS found for C14H20NO4S (M+H)+: m/z=298.

Workup

  1. customquenched with acetic acid (1 mL)
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-946b19189dec44ed98a0c34daa9e6b8b
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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