Boron trifluoride etherate → HCID 10286083, compound

HRID 2246987Notes

Reaction equation

HRID 2246987 reaction equation
COCOC.B(F)(F)F.[CH3:10]COCC.[C:15]([N:18]1[CH2:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[NH:21][CH2:20][CH2:19]1)(=[O:17])[CH3:16].[CH:29]1[CH2:33][CH2:32][CH2:31][CH:30]=1.[OH-].[Na+]>C(Cl)Cl>[C:15]([N:18]1[CH2:24][C:23]2=[C:22]3[C:28](=[CH:27][CH:26]=[CH:25]2)[CH:30]2[CH2:31][CH2:32][CH2:33][CH:29]2[CH2:10][N:21]3[CH2:20][CH2:19]1)(=[O:17])[CH3:16]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherate2×HCID 8020Dimethoxymethane2×HCID 8882Cyclopentene2×HCID 14798Sodium HydroxideHCID 114354344-Acetyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine

Product 1

HCID 10286083HCID 10286083, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dimethoxymethane (34.9 mL, 394 mmol) was dissolved in methylene chloride (800 mL) and cooled to 0° C. in a ice bath. To this solution, boron trifluoride etherate (18.3 mL, 144 mmol) was added and the reaction was stirred for 30 minutes. Subsequently, a solution of 4-Acetyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (25 g, 131 mmol) in methylene chloride (500 mL) was added to the reaction through an addition funnel over several hours. During the course of this addition, cyclopentene (23.1 mL, 263 mmol) was added to the reaction. The reaction was allowed to warm to room temperature overnight. Additional portions of the dimethoxymethane, boron trifluoride etherate and cyclopentene were added as necessary to facilitate greater conversion. The reaction was neutralized with NaOH and extracted with methylene chloride and the organic layer was washed with saturated brine solution. After drying with MgSO4, the solvent was evaporated in vacuo and the product was purified by flash chromatography (silica gel, ethyl acetate:hexanes 55:45 with 1% triethylamine) to provide 7.4 grams of the title compound.

Workup

  1. additionwas added to the reaction
  2. temperatureto warm to room temperature overnight
  3. extractionextracted with methylene chloride
  4. washthe organic layer was washed with saturated brine solution
  5. dry with materialAfter drying with MgSO4
  6. customthe solvent was evaporated in vacuo
  7. customthe product was purified by flash chromatography (silica gel, ethyl acetate:hexanes 55:45 with 1% triethylamine)

Sources & evidence

ORD record
ord-eba6653e7a2e4cfa9f5a41276e51de8b
Source dataset
uspto-grants-2010_03
Patent number
US07687620B2

Reaction notes

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