Triethylamine → HCID 68533153, compound

HRID 657541Notes

Reaction equation

HRID 657541 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C@@H:8]([CH2:14]N)[CH2:7]2.C([N:18](CC)CC)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>ClCCl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C@H:8]([CH2:14][C:23]1([C:26]([NH2:18])=[O:27])[CH2:25][CH2:24]1)[CH2:7]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 44820357HCID 44820357, compound

Product 1

HCID 68533153HCID 68533153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4.6 g (20 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}amine hydrochloride in 60 mL of dichloromethane, at ambient temperature, there are added, all at once, 6.1 mL (44 mmol/2.2 eq.) of triethylamine and stirring is carried out for about 30 minutes. There are then added dropwise, over 40 minutes, 2 mL (22 mmol/1.1 eq.) of cyclopropanecarboxylic acid chloride. The mixture is then stirred at ambient temperature for 1 hour 30 minutes and is then transferred to a separating funnel; 60 mL of dichloromethane are added and successive washing with 40 mL of water, two 40 mL quantities of 1N hydrochloric acid, two 40 mL quantities of saturated aqueous sodium hydrogen carbonate solution and 40 mL of water are carried out. After drying over magnesium sulphate, filtration and concentration, the desired product is collected.

Workup

  1. additionThere are then added dropwise, over 40 minutes
  2. customis then transferred to a separating funnel
  3. washsuccessive washing with 40 mL of water, two 40 mL quantities of 1N hydrochloric acid, two 40 mL quantities of saturated aqueous sodium hydrogen carbonate solution and 40 mL of water
  4. dry with materialAfter drying over magnesium sulphate, filtration and concentration
  5. customthe desired product is collected

Sources & evidence

ORD record
ord-ac9dd73e7bd34fc78eff56650bc42830
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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