(3-Cyclohexylcarbamoylmethyl-phenyl)-acetic acid → 2-[3-(2-Cyclohexylamino-ethyl)-phenyl]-ethanol

HRID 553302Notes

Reaction equation

HRID 553302 reaction equation
[CH:1]1([NH:7][C:8]([CH2:10][C:11]2[CH:12]=[C:13]([CH2:17][C:18](O)=[O:19])[CH:14]=[CH:15][CH:16]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>ClCCl>[CH:1]1([NH:7][CH2:8][CH2:10][C:11]2[CH:12]=[C:13]([CH2:17][CH2:18][OH:19])[CH:14]=[CH:15][CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 67165667(3-Cyclohexylcarbamoylmethyl-phenyl)-acetic acid

Product 1

HCID 671649572-[3-(2-Cyclohexylamino-ethyl)-phenyl]-ethanolYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Cyclohexylcarbamoylmethyl-phenyl)-acetic acid (620 mg) was dissolved in dry dichloromethane (25 mL) and treated with borane-methyl sulphide complex (2M, 12 mL) at room temperature. The reaction was stirred at room temperature for 1 hour and at reflux for a further 1 hour. The mixture was cooled, quenched with methanol and treated with 2M hydrochloric acid (25 mL). The acidified mixture was heated at reflux for 10 minutes, cooled and basified with 2M sodium hydroxide. The basic mixture was extracted with dichloromethane (2×50 mL). The organic extracts were combined, dried over anhydrous sodium sulphate, filtered and concentrated to yield 500 mg of the sub-titled compound as an oil.

Workup

  1. additiontreated with borane-methyl sulphide complex (2M, 12 mL) at room temperature
  2. temperatureat reflux for a further 1 hour
  3. temperatureThe mixture was cooled
  4. customquenched with methanol
  5. additiontreated with 2M hydrochloric acid (25 mL)
  6. temperatureThe acidified mixture was heated
  7. temperatureat reflux for 10 minutes
  8. temperaturecooled
  9. extractionThe basic mixture was extracted with dichloromethane (2×50 mL)
  10. dry with materialdried over anhydrous sodium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-691e48f7cfc74508a5272d71a8d5abd4
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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