Salicylaldehyde → cis-5-(Methoxycarbonyl)piperidine-2-carboxylic Acid

HRID 466588Notes

Reaction equation

HRID 466588 reaction equation
[NH:1]1[CH2:6][C@H:5]([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:3][C@@H:2]1[C:11]([O:13]C)=[O:12].C(=O)C1C(=CC=CC=1)O>C(O)(=O)C>[CH3:10][O:9][C:7]([C@H:5]1[CH2:6][NH:1][C@@H:2]([C:11]([OH:13])=[O:12])[CH2:3][CH2:4]1)=[O:8]

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 13413095HCID 13413095, compound

Product 1

HCID 21782947cis-5-(Methoxycarbonyl)piperidine-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Dimethyl cis-piperidine-2,5-dicarboxylate (112 g, 0.56 mol), salicylaldehyde (3 ml, 0.056 mol) and glacial acetic acid (600 ml) were combined and the resulting mixture heated at about 100° C. for 60 hours. The mixture was cooled, than stripped in vacuo to a thick oil from which 61.7 g (59%) of title products crystallized upon stirring with 800 ml of isopropyl alcohol. Product ratio was determined by 1H-NMR (D2O, 300 MHz), a peak at 3.13 ppm (t, 1H, J=14.5 Hz) being diagnostic of trans, and a peak at 3.33 ppm (dd, 1H) being diagnostic of cis.

Workup

  1. temperatureThe mixture was cooled
  2. customcrystallized

Sources & evidence

ORD record
ord-913d9023941e41ed8e7a675d923b1f51
Source dataset
uspto-grants-1992_10
Patent number
US05157034

Reaction notes

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