Triethylamine → HCID 22903691, compound

HRID 1489160Notes

Reaction equation

HRID 1489160 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([CH2:20][N:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:18][OH:19])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([CH2:20][N:21]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([CH2:18][O:19][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22903658HCID 22903658, compound

Product 1

HCID 22903691HCID 22903691, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Mesyl chloride (2.7 ml) was added to a solution of 1-benzyl-3-(dibenzylaminomethyl)-3-hydroxymethylpyrrolidine (7.88 g) and triethylamine (5.5 ml) in chloroform (80 ml) under ice-cooling, and the mixture was stirred for 30 minutes under ice-cooling. The reaction mixture was sequentially washed with an aqueous solution of sodium hydrogencarbonate and water, dried, concentrated and purified by silica gel column chromatography to give 6.97 g of the object compound as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. washThe reaction mixture was sequentially washed with an aqueous solution of sodium hydrogencarbonate and water
  4. customdried
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-df2a225eece9484d9f2a5fdc57618ba0
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

Loading…