3-Bromocyclohexene → 2-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexene-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979345Notes

Reaction equation

HRID 1979345 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][CH:3]1[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].Br[CH:23]1[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]1.C(=O)(O)[O-].[Na+]>CO>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([CH:28]2[CH2:27][CH2:26][CH2:25][CH:24]=[CH:23]2)[CH2:4][CH:3]1[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 1370573-BromocyclohexeneHCID 516892Sodium BicarbonateHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212015412-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexene-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 35.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (3.00 g) obtained from Referential Example 7 was suspended in methanol (30 ml), 90% 3-bromocyclohexene (6.08 g) and sodium bicarbonate (2.85 g) were added, and the mixture was stirred for 5 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water (100 ml) was added to the residue, extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 1.36 g of the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water (100 ml)
  2. additionwas added to the residue
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d14a4ec671804bc38c5154b01bb4ca8e
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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