Ethyl 4-piperidinecarboxylate → HCID 67035398, compound

HRID 1944247Notes

Reaction equation

HRID 1944247 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][N:14]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(O[K])(C)(C)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 70770Ethyl 4-piperidinecarboxylateHCID 634876Binap, (A+-)-HCID 151690002-Chloro-5-methoxypyridineHCID 178418922HCID 178418922, compound

Product 1

HCID 67035398HCID 67035398, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of piperidine-4-carboxylic acid ethyl ester (0.52 g, 3.34 mmol) and 2-chloro-5-methoxy-pyridine in 10 mL of toluene was added (13 mg, 0.057 mmol) of Pd(II) acetate, (17 mg, 0.027 mmol) of BINAP and tBuOK (0.44 g, 3.90 mmol). The mixture was heated at 120° C. for two hours, concentrated under vacuo and the residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1:2) yielding 0.17 g (24%) of the title compound as a light yellow oil. ES-MS m/e: 265.3 (M-41′).

Workup

  1. concentrationconcentrated under vacuo
  2. customthe residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1:2)

Sources & evidence

ORD record
ord-c10c6e2bda164b1f862527c062d2c03a
Source dataset
uspto-grants-2013_03
Patent number
US08394834B2

Reaction notes

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