Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 21196718, compound

HRID 1066889Notes

Reaction equation

HRID 1066889 reaction equation
O=[C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5][CH2:4][CH:3]1[CH2:11][CH:12]=O.[C:14]([NH:17][CH2:18][CH2:19][NH2:20])(=[O:16])[CH3:15].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[N:20]1([CH2:19][CH2:18][NH:17][C:14](=[O:16])[CH3:15])[C:2]2[C:3](=[CH:4][CH:5]=[C:6]3[S:7][CH:8]=[CH:9][C:10]3=2)[CH:11]=[CH:12]1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 66082N-(2-aminoethyl)acetamideHCID 21196697HCID 21196697, compound

Product 1

HCID 21196718HCID 21196718, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 4.20 g of sodium periodate was added gradually to a mixture of 1.80 g of 5-allyl-4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene, 25 mg of osmium tetraoxide, 15 ml of water and 45 ml of dioxane, while keeping the reaction mixture at 24 to 26° C., and then the mixture was stirred at room temperature for 3 hours. After extraction of the reaction mixture with ethyl acetate, the organic layers were combined, washed with 2% sodium thiosulfate aqueous solution, water and brine in that order and then dried with anhydrous magnesium sulfate. After removal of the drying agent, the solvent was concentrated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography to give 1.33 g of (4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-5-yl)acetaldehyde. A 1.32 g of the aldehyde compound and 1.39 g of N-acetylethylenediamine were dissolved in 50 ml of toluene. Then, 10 mg of camphorsulfonic acid was added, and the mixture was heated under reflux for 3 hours while removing the produced water. After cooling, the reaction solution was poured into ice-cooled saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layers were combined, the drying agent was removed by filtration and then the solvent was concentrated under a reduced pressure to give 1.38 g of N-(2-(4,5-dihydro-1H-thieno[2,3-g]indol-1-yl)ethyl]acetaamide. From this compound, N-[2-(1H-thieno[2,3-g]indol-1-yl)ethyl]acetamide was obtained in the similar manner as described in Reference Example 60.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customwhile removing the produced water
  4. temperatureAfter cooling
  5. additionthe reaction solution was poured into ice-
  6. temperaturecooled saturated sodium bicarbonate aqueous solution
  7. extractionextracted with ethyl acetate
  8. customthe drying agent was removed by filtration
  9. concentrationthe solvent was concentrated under a reduced pressure
  10. customto give 1.38 g of N-(2-(4,5-dihydro-1H-thieno[2,3-g]indol-1-yl)ethyl]acetaamide

Sources & evidence

ORD record
ord-8d2d48bf3b4b40ada541da413b5a0c56
Source dataset
uspto-grants-2001_06
Patent number
US06245796B1

Reaction notes

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