Triethylamine → N-([(7S)-3, 4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-methyl}-2,2,2-trifluoroacetamide

HRID 657542Notes

Reaction equation

HRID 657542 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH2:14])[CH2:6]2.C(N(CC)CC)C.[F:22][C:23]([F:30])([F:29])[C:24](OCC)=[O:25]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH:14][C:24](=[O:25])[C:23]([F:30])([F:29])[F:22])[CH2:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 115066164,5-Dimethoxy-1-(aminomethyl)benzocyclobutane, (S)-

Product 1

HCID 86628625N-([(7S)-3, 4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-methyl}-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.9 g (15 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}amine in 7.5 mL of methanol, at ambient temperature, there are added, all at once, 2.1 mL (15 mmol/1 eq.) of triethylamine, and then, dropwise, over 20 minutes, 2.3 mL (19 mmol/1.25 eq.) of ethyl trifluoroacetate. Stirring is carried out at ambient temperature for 2 hours, followed by evaporating to dryness. The residue is taken up in 100 mL of dichloromethane, and washing with 50 mL of 1N hydrochloric acid and then 50 mL of water and drying over magnesium sulphate are carried out. After filtration and concentration, the desired product is collected.

Workup

  1. customby evaporating to dryness
  2. washwashing with 50 mL of 1N hydrochloric acid
  3. dry with material50 mL of water and drying over magnesium sulphate
  4. filtrationAfter filtration and concentration
  5. customthe desired product is collected

Sources & evidence

ORD record
ord-1f9e5c1d61c145b38d29b5dd563bf9c6
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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