p-Toluenesulfonic acid → 1-{1-[(1,1-Dioxido isothiazolidin-2-yl)methyl]tricyclo[3.3.1.03,7]non-3-yl}ethanone

HRID 1015538Notes

Reaction equation

HRID 1015538 reaction equation
[CH3:1][C:2]1([C:7]23[CH2:14][CH:13]4[CH2:15][C:9]([CH2:16][N:17]5[CH2:21][CH2:20][CH2:19][S:18]5(=[O:23])=[O:22])([CH2:10][CH:11]2[CH2:12]4)[CH2:8]3)OCC[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.CCOC(C)=O>[O:22]=[S:18]1(=[O:23])[CH2:19][CH2:20][CH2:21][N:17]1[CH2:16][C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:10]1)[C:7]([C:2](=[O:3])[CH3:1])([CH2:14]3)[CH2:8]2

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 670178842-{[3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methyl}isothiazolidine 1,1-dioxide

Product 1

HCID 670178461-{1-[(1,1-Dioxido isothiazolidin-2-yl)methyl]tricyclo[3.3.1.03,7]non-3-yl}ethanoneYield 92.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of the compound obtained by Step I (0.68 g, 2.0 mmol) and p-toluenesulfonic acid (38 mg, 0.2 mmol) in acetone (8 mL) was refluxed for 4 h. The reaction mixture was diluted with EtOAc and washed with 10% aq. NaHCO3 and brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure to obtain 1-{1-[(1,1-dioxido isothiazolidin-2-yl)methyl]tricyclo[3.3.1.03,7]non-3-yl}ethanone (0.55 g) in 92% yield as a viscous liquid.

Workup

  1. washwashed with 10% aq. NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-95fc627dd69943e69a9a58b7ef0429bb
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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