Ethyl nipecotate → HCID 68575353, compound

HRID 720895Notes

Reaction equation

HRID 720895 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[O:12]1[CH2:14][C@@H:13]1[CH2:15][O:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2>C(O)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:14][CH:13]([OH:12])[CH2:15][O:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][CH:21]=[N:22]3)[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 98969Ethyl nipecotateHCID 11735808(R)-5-(Oxiran-2-ylmethoxy)quinoline

Product 1

HCID 68575353HCID 68575353, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine-3-carboxylic acid ethyl ester (43) (1.0 g; 6.36 mmol) and (R)-5-oxiranylmethoxy-quinoline (2) (1.28 g; 6.36 mmol) are combined in 10 mL of absolute ethanol. The mixture is heated at reflux for 16 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is chromatographed on silica gel (1:1 acetone:hexanes) affording the desired product (44) as an oil. ESMS:MH+ 359

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 16 hours
  3. concentrationthe solution is concentrated in vacuo at 40° C
  4. customThe residue is chromatographed on silica gel (1:1 acetone:hexanes)

Sources & evidence

ORD record
ord-862efd50f1e04dddbaae148c5d536361
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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