Ethyl nipecotate → HCID 69693967, compound

HRID 489899Notes

Reaction equation

HRID 489899 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:23]1[CH2:33][CH2:32][CH2:31][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24]1>CN(C)C=O.O>[CH2:29]([O:28][C:26]([CH:25]1[CH2:31][CH2:32][CH2:33][N:23]([CH:16]2[CH2:17][N:14]([CH:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:15]2)[CH2:24]1)=[O:27])[CH3:30]

Participants

5

Reactant 2

HCID 98969Ethyl nipecotateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 69693967HCID 69693967, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Methanesulfonic acid 1-benzhydryl-azetidin-3-yl ester (A. G. Anderson, Jr. and R. Lok, J. Org. Chem., 1972, 37, 3953)(2.22 g, 7 mmol) and ethyl nipecotate (1.0 g, 6.37 mmol) were dissolved in dimethylformamide (3 mL) and heated at 110° C. for 1 hr. The mixture was cooled to ambient temperature, diluted with water and extracted with dichloromethane (3×15 mL). The extract was dried over anhydrous magnesium sulfate and the solvent removed under vacuum to give an impure sample of 1-(1-benzhydryl-azetidin-3-yl)-piperidine-3-carboxylic acid ethyl ester (2.91 g).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionextracted with dichloromethane (3×15 mL)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-0d24745083d645bcb53da76c92776519
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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