Triethylamine → HCID 86646805, compound

HRID 1691585Notes

Reaction equation

HRID 1691585 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH2:17][CH2:18][OH:19])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH3:37][S:38]([O:19][CH2:18][CH2:17][CH:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)(=[O:40])=[O:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86646806HCID 86646806, compound

Product 1

HCID 86646805HCID 86646805, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-1-(3-(2-morpholinoethoxyphenyl)-3-(3,4-dimethoxyphenyl)propan-1-ol (0.4 g, 1.0 mmol) in dichloromethane (5.0 mL) under N2 was added triethylamine (0.4 g, 4.0 mmol). The solution was then cooled to 0° C., methanesulfonyl chloride (0.28 g, 2.5 mmol) was added, and the reaction was stirred at 0° C. for 1.5 h. Ice cold water (5.0 mL) was added to the reaction mixture and it was extracted with dichloromethane. The combined organic extract was washed with a cold solution of ammonium chloride, brine, then dried over anhydrous MgSO4. Evaporation of the solvent afforded (S)-1-(3-(2-morpholinoethoxyphenyl)-3-(3,4-dimethoxyphenyl)propyl methanesulfonate (0.42 g, 88% yield).

Workup

  1. extractionwas extracted with dichloromethane
  2. extractionThe combined organic extract
  3. washwas washed with a cold solution of ammonium chloride, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-258d108f5b3949249e723b29e94571ee
Source dataset
uspto-grants-2012_04
Patent number
US08153785B2

Reaction notes

Loading…