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

HRID 217183노트

반응식

HRID 217183 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-96dc6d913fc24e5f8ab970f5eef3eb27
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193359B2

반응 노트

불러오는 중…