2-Bromoethanol → 2-[{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]ethanol

HRID 657548Notes

Reaction equation

HRID 657548 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][NH:14][CH3:15])[CH2:6]2.BrC[CH2:18][OH:19].[C:20](=O)([O-])[O-].[K+].[K+]>C(#N)C>[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][N:14]([CH3:20])[CH2:15][CH2:18][OH:19])[CH2:6]2

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 11499437(S)-1-(3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)-N-methylmethanamine

Product 1

HCID 689736902-[{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]ethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At ambient temperature, 1.04 g (5 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}methylamine, 0.44 mL (6 mmol/1.2 eq.) of 2-bromoethanol and 2.07 g (15 mmol/3 eq.) of potassium carbonate are mixed into 10 mL of acetonitrile. Refluxing is carried out overnight, followed by drying. The residue is taken up in dichloromethane, washed with water and dried over magnesium sulphate to yield, after concentration, the desired product.

Workup

  1. temperatureRefluxing
  2. customby drying
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customto yield
  6. concentrationafter concentration

Sources & evidence

ORD record
ord-97b2131e61384ba9a12ce2533b9013f3
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

Loading…