Methanol → 9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

HRID 440742Notes

Reaction equation

HRID 440742 reaction equation
O=[C:2]1[NH:8][C:7]2[S:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]2[CH:12]=[CH:13][CH:14]=[C:3]12.[B].CSC.CO>O1CCCC1>[S:9]1[C:7]2[NH:8][CH2:2][C:3]3[N:4]([CH:12]=[CH:13][CH:14]=3)[CH2:5][C:6]=2[CH:11]=[CH:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 110418649-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]-thieno[2,3-e][1,4]diazepine

Product 1

HCID 218371599,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 7.0 g of 9-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepin in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10 molar boron-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours. The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2N NaOH. The mixture is refluxed 5 hours and filtered. The solid is extracted with dichloromethane and the extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed in vacuo to give the desired product as a solid.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customThe volatiles are removed under vacuum
  3. additionTo the residue is added 100 ml of 2N NaOH
  4. temperatureThe mixture is refluxed 5 hours
  5. filtrationfiltered
  6. extractionThe solid is extracted with dichloromethane
  7. washthe extract is washed with 2N citric acid, water
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-f790d911ffa847dea3c8f7b868b2a658
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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