Benzyl Bromide → HCID 58598888, compound

HRID 1020330Notes

Reaction equation

HRID 1020330 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C(NC(=O)[O-])C.[OH:21][C:22]1[CH:23]=[CH:24][C:25]2[CH:26]([CH3:34])[CH:27]3[CH2:31][NH:30][CH2:29][CH:28]3[C:32]=2[CH:33]=1>CC#N>[CH2:1]([O:21][C:22]1[CH:23]=[CH:24][C:25]2[CH:26]([CH3:34])[CH:27]3[CH2:31][NH:30][CH2:29][CH:28]3[C:32]=2[CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86602864N-Ethylcarbamate 5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 58598888HCID 58598888, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl bromide (15 μL, 0.12 mmol) and K2CO3 (70 mg, 0.5 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydro indeno[1,2-c]pyrrole (26 mg, 0.1 mmol) in CH3CN (2 mL). The resulting mixture was stirred overnight at 80° C. The reaction was cooled to room temperature, concentrated by rotary evaporation and taken up in H2O (2.5 mL). The product was extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over MgSO4 and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C22H25NO3+H: 352, observed: 352.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated by rotary evaporation
  3. extractionThe product was extracted with ethyl acetate (3×5 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e1a40377781746eda59b92cb4b2dbb42
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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