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

HRID 217183ノート

反応式

HRID 217183 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-96dc6d913fc24e5f8ab970f5eef3eb27
出典データセット
uspto-grants-2012_06
特許番号
US08193359B2

反応ノート

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