Triethylamine → HCID 10446037, compound

HRID 1494074Notes

Reaction equation

HRID 1494074 reaction equation
O[CH2:2][CH2:3][CH:4]([CH2:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[CH2:20]([N:22](CC)CC)C.CS(Cl)(=O)=O.[C-]#N.[K+]>C(Cl)Cl.CS(C)=O>[C:20]([CH2:2][CH2:3][CH:4]([CH2:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])#[N:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 31297Methanesulfonyl chlorideHCID 11777635HCID 11777635, compound

Product 1

HCID 10446037HCID 10446037, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.8 g (3.0 mmol) of methyl 7-hydroxy-5-[2-(3-pyridyl)ethyl]-heptanoate in 3 ml methylene chloride is cooled to 0° and 0.52 mL (3.7 mmol) triethylamine is added followed by 0.26 mL (3.3 mL) methanesulfonyl chloride. The reaction mixture is stirred at 0° for 30 minutes and then 1.65 g (25 mmol) finely powdered potassium cyanide is added followed by 15 mL dimethyl sulfoxide. After stirring for 30 minutes the cold bath is removed and the mixture is stirred at room temperature for 18 hours. The reaction mixture is poured on to saturated aqueous ammonium chloride solution and then extracted with ethyl acetate (3×70 mL). Combined organic phase is washed with water (4×60 mL), brine (60 mL) and dried (MgSO4), filtered and evaporated to give an oil which is purified by flash chromatography to give both the desired methyl 7-cyano-5-[2-(3 -pyridyl)ethyl]-heptanoate and the mesylate of the starting alcohol. The mesylate is subjected to the cyanide displacement conditions described above to yield additional methyl 7-cyano-5-[2-(3-pyridyl)-ethyl]-heptanoate.

Workup

  1. stirringAfter stirring for 30 minutes the cold bath
  2. customis removed
  3. stirringthe mixture is stirred at room temperature for 18 hours
  4. additionThe reaction mixture is poured on to saturated aqueous ammonium chloride solution
  5. extractionextracted with ethyl acetate (3×70 mL)
  6. washCombined organic phase is washed with water (4×60 mL), brine (60 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto give an oil which
  11. customis purified by flash chromatography

Sources & evidence

ORD record
ord-2ac4288471394be8975f26b4d7f86398
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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