Sodium Methoxide → HCID 68795785, compound

HRID 2065773Notes

Reaction equation

HRID 2065773 reaction equation
C[O:2][C:3]([C@@H:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:9][CH2:8][N:7]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6]1)=[O:4].C[O-].[Na+]>C1(C)C=CC=CC=1>[C:21]([O:20][C:18]([N:7]1[CH2:8][CH2:9][C@@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C@H:5]([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68750810HCID 68750810, compound

Product 1

HCID 68795785HCID 68795785, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (3R,4R)-4-o-tolyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (200 mg) and sodium methoxide (65 mg) in anhydrous toluene (6 mL) was heated at reflux over night. After cooling to room temperature the reaction mixture was quenched with water and concentrated in vacuo. The residue was dissolved in a mixture of 1,4-dioxane (3 mL) and 2 M aqueous sodium hydroxide solution (3 mL). After stirring at RT for 5 h the mixture was diluted with water and washed with two portions of tert-butyl methyl ether. The aqueous layer was cooled to 0° C., acidified to pH 1-2 with ice-cold 1 M aqueous KHSO4 solution and extracted with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered and evaporated to give (3S,4R)-4-o-tolyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester as a white solid, MS: 318.4 ([M−H])−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night
  3. customwas quenched with water
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in a mixture of 1,4-dioxane (3 mL) and 2 M aqueous sodium hydroxide solution (3 mL)
  6. additionwas diluted with water
  7. washwashed with two portions of tert-butyl methyl ether
  8. temperatureThe aqueous layer was cooled to 0° C.
  9. extractionextracted with ethyl acetate
  10. dry with materialThe combined organic layers were dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-fd0d420389ed41abb977ab17c50373f8
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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