Potassium Carbonate → 4-(2-Furo[2,3-c]pyridin-2-ylvinyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 217183Notes

Reaction equation

HRID 217183 reaction equation
C([O-])([O-])=O.[K+].[K+].[I-].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[O:41]1[C:45]2=[CH:46][N:47]=[CH:48][CH:49]=[C:44]2[CH:43]=[C:42]1[CH:50]=O>C(Cl)Cl>[C:8]([O:12][C:13]([N:15]1[CH2:16][CH2:17][CH:18]([CH:21]=[CH:50][C:42]2[O:41][C:45]3=[CH:46][N:47]=[CH:48][CH:49]=[C:44]3[CH:43]=2)[CH2:19][CH2:20]1)=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 642129Furo(2,3-c)pyridine-2-carbaldehydeHCID 18187633((1-(tert-Butoxycarbonyl)piperidin-4-yl)methyl)triphenylphosphonium iodide

Product 1

HCID 689395454-(2-Furo[2,3-c]pyridin-2-ylvinyl)piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

K2CO3 (122 mg, 0.88 mmol) and 18C6 (catalytic amount) were added to a stirred solution of (1-tert-butoxycarbonylpiperidin-4-ylmethyl)triphenylphosphonium iodide (491 mg, 0.88 mmol) and furo[2,3-c]pyridine-2-carbaldehyde (65 mg, 0.44 mmol) in anhydrous CH2Cl2 (10 mL). After 64 h, the reaction mixture was partitioned between CH2Cl2 (50 mL) and H2O (20 mL). The aqueous phase was further extracted with CH2Cl2 (2×20 mL), then the combined organic extracts were washed with H2O (20 mL) and brine (20 mL), before being dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (IH-EtOAc, 7:3) afforded 4-(2-furo[2,3-c]pyridin-2-ylvinyl)piperidine-1-carboxylic acid tert-butyl ester: m/z (ES+)=329.2 [M+H]+. This alkene (30 mg, 91 μmol) was hydrogenated, as described above in Example 18, to yield the title compound: RT=2.86 min; m/z (ES+)=331.2 [M+H]+.

Workup

  1. customthe reaction mixture was partitioned between CH2Cl2 (50 mL) and H2O (20 mL)
  2. extractionThe aqueous phase was further extracted with CH2Cl2 (2×20 mL)
  3. washthe combined organic extracts were washed with H2O (20 mL) and brine (20 mL)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationFiltration, solvent evaporation, and flash chromatography (IH-EtOAc, 7:3)

Sources & evidence

ORD record
ord-96dc6d913fc24e5f8ab970f5eef3eb27
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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