O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → 2-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate

HRID 15187

Reaction equation

HRID 15187 reaction equation
[C:1]([O:9][CH:10]1[CH2:16][CH2:15][CH:14]2[CH:11]1[CH2:12][C:13]2=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:30])(=O)=O>C(Cl)Cl>[C:1]([O:9][CH:10]1[CH:11]2[CH:14]([C:13](=[O:17])[NH:30][CH2:12]2)[CH2:15][CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([O:9][CH:10]1[CH:11]2[CH:14]([NH:30][C:13](=[O:17])[CH2:12]2)[CH2:15][CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 592595756-Oxobicyclo[3.2.0]heptan-2-yl benzoate

Product 2

HCID 592595601-Oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoateHCID 592595712-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoateYield 133.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of compound 1H (500 mg, 2.2 mmol) in CH2Cl2 (5 mL) was added a solution of O-mesitylenesulfonylhydroxylamine (650 mg, 3 mmol) in CH2Cl2 (2 mL) at −10° C., and the stirring was continued for 20 min between −10 to 0° C. It was concentrated, added to a mixed solvent of benzene and methanol (30 mL, 3:1) followed by a slurry of basic alumina (25 g) in methanol (20 mL). The reaction mixture was stirred at RT overnight, and alumina solid was removed by filtration. Purification by silica gel chromatography (5% to 100% EtOAc in hexanes, then 5% methanol in EtOAc) provide mixtures of the title compounds 1I and 1J (total 360 mg) as a yellow oil. MS (ES) m/z 246 [M+H]+.

Workup

  1. concentrationIt was concentrated
  2. additionadded to a mixed solvent of benzene and methanol (30 mL, 3:1)
  3. customalumina solid was removed by filtration
  4. customPurification by silica gel chromatography (5% to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-69d09e97128d4e6b92c02884fe908ded
Source dataset
uspto-grants-2010_06
Patent number
US07732480B2

Linked notes

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