Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 10444800, compound

HRID 2427415Notes

Reaction equation

HRID 2427415 reaction equation
[C:1]([CH:4]([CH2:15][CH2:16][CH2:17][SH:18])[CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])(O)=[O:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[O:2]=[C:1]1[CH:4]([CH2:5][C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=[O:10])[CH2:15][CH2:16][CH2:17][S:18]1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 9878510HCID 9878510, compound

Product 1

HCID 10444800HCID 10444800, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(2-carboxy-5-mercaptopentyl)benzoic acid (5.12 g, 20 mmol) and 10-camphorsulfonic acid (500 mg) in toluene (30 mL) was refluxed for 6 hours. The liberated water was removed using a Dean-Stork azeotropic adapter. Toluene was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (EtOAc/hexanes, 1:4). Fractions containing the product were collected, evaporated and recrystallized from EtOAc/hexanes to afford 3.2 g of 3-[(2-oxotetrahydro-2H-thiopyran-3-yl)methyl]benzoic acid as a white solid (67% yield): 1H NMR (CDCl3) δ 1.58-1.68 (m, 1H), 1.90-2.02 (m, 2H), 2.04-2.13 (m, 1H), 2.68 (m, 1H), 2.78-2.86 (m, 1H), 3.08-3.19 (m, 2H), 3.37-3.44 (m, 1H), 7.38-7.48 (m, 2H), 7.93 (brs, 1H), 7.94-8.02 (m, 1H); 13C NMR (CDCl3) δ 22.6, 27.8, 31.1, 36.8, 52.0, 128.8, 129.2, 129.8, 131.3, 135.3, 140.1, 172.6, 203.7. Analysis calculated for C13H14O3S: C, 62.38; H, 5.64; S, 12.81. Found: C, 62.19; H, 5.65; S, 12.59.

Workup

  1. customThe liberated water was removed
  2. distillationToluene was then distilled off under reduced pressure
  3. customthe residue was purified by silica gel chromatography (EtOAc/hexanes, 1:4)
  4. additionFractions containing the product
  5. customwere collected
  6. customevaporated
  7. customrecrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-b996ca5cf23e4521a80d5d356c7fba63
Source dataset
uspto-grants-2011_06
Patent number
US07968593B2

Reaction notes

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