Ethanol → Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate

HRID 128058Notes

Reaction equation

HRID 128058 reaction equation
S(Cl)(Cl)=O.[CH3:5][C@@H:6]1[CH2:11][CH2:10][NH:9][C@@H:8]([C:12]([OH:14])=[O:13])[CH2:7]1.[CH2:15](O)[CH3:16]>>[CH3:5][C@@H:6]1[CH2:11][CH2:10][NH:9][C@@H:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 5288786(2R,4R)-4-methylpiperidine-2-carboxylic acid

Product 1

HCID 10313307Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate

Procedure

Thionyl chloride (128.6 g) added dropwise to a stirred suspension of (2R,4R)-4-methyl-2-piperidinecarboxylic acid (51.6 g) in absolute ethyl alcohol (690 ml) below 30° C. and stirring continued for 1 hr. at room temperature and then for 1 hr. under reflux. After evaporation of the solvent, the residue was dissolved in benzene (500 ml), washed with 5% K2CO3 solution (100 ml) and saturated NaCl solution (200 ml), and dried over anhydrous Na2SO4. Upon evaporation of benzene, the residue was distillated in vacuo to give ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate (57.4 g), b.p. 83°-5° C./7 mm Hg, [α]D22 =-24.0 (C=5 in EtOH), Analysis Calcd. for C9H17NO2 (percent): C, 63.13, H, 10.00, N, 8.18 Found (percent): C, 63.20, H, 9.96, N, 8.12.

Workup

  1. waitat room temperature and then for 1 hr
  2. temperatureunder reflux
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue was dissolved in benzene (500 ml)
  5. washwashed with 5% K2CO3 solution (100 ml) and saturated NaCl solution (200 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customUpon evaporation of benzene

Sources & evidence

ORD record
ord-230f52cd5b084811a8bbbe7a377c0d4b
Source dataset
uspto-grants-1981_03
Patent number
US04258192

Reaction notes

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