Triethylamine → HCID 68734256, compound

HRID 2382199Notes

Reaction equation

HRID 2382199 reaction equation
[C:1]1([CH:7]([C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:27][O:28][C:29](=[O:32])[CH2:30]Br>ClCCl>[C:1]1([CH:7]([C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[CH:8]2[CH2:12][CH2:11][N:10]([CH2:30][C:29]([O:28][CH3:27])=[O:32])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 68734802HCID 68734802, compound

Product 1

HCID 68734256HCID 68734256, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-(phenyl(m-tolyl)methyl)pyrrolidine (3.0 g, 12 mmol) and triethylamine (1.8 mL, 12.9 mmol) in dichloromethane (30 mL) was stirred at 0° C. for 10 min, and then methylbromoacetate (1.5 mL, 15.8 mmol) was added dropwise. After stirring the reaction mixture at 0° C. for 3 h, reaction mixture was warmed to room temperature and concentrated under reduced pressure. To the residue was added water and the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product. The crude product was dissolved in dichloromethane and precipitated with diethyl ether to afford 1.6 g of methyl 2-(3-(phenyl(m-tolyl)methyl)pyrrolidin-1-yl)acetate.

Workup

  1. customreaction mixture
  2. temperaturewas warmed to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added water
  5. extractionthe aqueous layer was extracted with dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product
  9. customprecipitated with diethyl ether

Sources & evidence

ORD record
ord-2408f900bd3241da915962e99f6160e9
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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