Triethylamine → Methyl 8-methylsulfonyloxy-2,2-dimethyl-4-[3-(3-pyridyl)propyl]-octanoate

HRID 465570Notes

Reaction equation

HRID 465570 reaction equation
[CH3:1][C:2]([CH3:23])([CH2:7][CH:8]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:7][C:2]([CH3:23])([CH3:1])[C:3]([O:5][CH3:6])=[O:4])(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10018995Methyl 2,2-dimethyl-4-[3-(3-pyridyl)propyl]8-hydroxyoctanoate

Product 1

HCID 10092354Methyl 8-methylsulfonyloxy-2,2-dimethyl-4-[3-(3-pyridyl)propyl]-octanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.28 g (4 mmol) of methyl 2,2-dimethyl-4-[3-(3-pyridyl)propyl]8-hydroxyoctanoate in 20 ml methylene chloride at 0° is added 0.9 ml (6.5 mmol) triethylamine followed by 0.4 ml (5.2 mmol) methylsulfonyl chloride. After 1 h, the reaction mixture is diluted with methylene chloride and washed with saturated sodium bicarbonate, water and brine. The organic phase is dried, filtered and evaporated to give methyl 8-methylsulfonyloxy-2,2-dimethyl-4-[3-(3-pyridyl)propyl]-octanoate as an oil.

Workup

  1. washwashed with saturated sodium bicarbonate, water and brine
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-296709e749cc44b0bf65153640a48d2e
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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