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

HRID 1494113Notes

Reaction equation

HRID 1494113 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11][CH3:12])=[O:10])(=[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 8-hydroxy-2,2-dimethyl-4-[3-(3-pyridyl)propyl]octanoate in 20 mL methylene chloride at 0° C. is added 0.9 mL (6.5 mmol) triethylamine followed by 0.4 mL (5.2 mmol) methanesulfonyl chloride. After 1 hour, the reaction 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-methanesulfonyloxy-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-decdd92586264485ba67d424174068e1
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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