Water → 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine

HRID 976372Notes

Reaction equation

HRID 976372 reaction equation
[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.B#B.CSC.O.[OH-].[Na+]>O1CCCC1>[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 123593406,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-oneHCID 22038413Diborane dimethylsulfide

Product 1

HCID 123593416,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepineYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.070 g of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-6-one in 2 ml of tetrahydrofuran is added 0.45 ml of a 2.0M solution of diborane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 3 hours, poured into water and made basic with 2N NaOH. The tetrahydrofuran is removed under vacuum and the residual aqueous mixture extracted with diethyl ether. The extract is washed with brine, dried (Na2SO4) and the solvent removed to give 0.065 g of a colorless oil; one spot by thin layer chromatography (silica gel) with ethyl acetate-hexane (1:2) as solvent (Rf 0.81).

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. customThe tetrahydrofuran is removed under vacuum
  3. extractionthe residual aqueous mixture extracted with diethyl ether
  4. washThe extract is washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-8b2a26cfe0734d588ff79f3675b6a12e
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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