Borane → Methyl 1-(Benzyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

HRID 1264602Notes

Reaction equation

HRID 1264602 reaction equation
[C:1]([N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][N:12]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:11]([C:31]([O:33][CH3:34])=[O:32])[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>O1CCCC1>[CH2:1]([N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][N:12]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH:11]([C:31]([O:33][CH3:34])=[O:32])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 186127381-Benzoyl-4-(4-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylic Acid Methyl Ester

Product 1

HCID 18612908Methyl 1-(Benzyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylateYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.20 g (0.416 mmol) of methyl 1-(benzoyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1 ,4]benzodiazepine-3-carboxylate and 4 ml of borane in tetrahydrofuran (1.0 M) was refluxed overnight and the solvent removed. To the residue was added 5 ml of CH2Cl2 and 5 ml of 2N HCl and the mixture stirred for 1 hour. The organic layer was separated and concentrated to dryness. The residue was chromatographed on thick layer silica gel plates with hexane-ethyl acetate (2:1) as solvent to give 0.140 g of a colorless oil; Mass spectrum (ES) 467.5 (M+H).

Workup

  1. temperaturewas refluxed overnight
  2. customthe solvent removed
  3. additionTo the residue was added 5 ml of CH2Cl2 and 5 ml of 2N HCl
  4. customThe organic layer was separated
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on thick layer silica gel plates with hexane-ethyl acetate (2:1) as solvent

Sources & evidence

ORD record
ord-af9193c74eb946ab83d881a483d6865e
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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