Methanol → 4,10-Dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

HRID 1940760Notes

Reaction equation

HRID 1940760 reaction equation
O=[C:2]1[NH:8][C:7]2=[CH:9][CH2:10][S:11][C:6]2=[CH:5][N:4]2[CH:12]=[CH:13][CH:14]=[C:3]12.B.CSC.CO>O1CCCC1>[S:11]1[C:6]2[CH2:5][N:4]3[CH:12]=[CH:13][CH:14]=[C:3]3[CH2:2][NH:8][C:7]=2[CH:9]=[CH:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 218371505-Oxo-4,5-dihydropyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

Product 1

HCID 218369694,10-Dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 7.0 g of 5-oxo-4,5-dihydro-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10 M borane-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 to give 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
  10. customto give a solid

Sources & evidence

ORD record
ord-3ae517f3e45e42c4b03d00982aa12966
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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