3-Phenylpentane → HCID 70197121, 화합물

HRID 1276507노트

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HRID 1276507 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]([NH2:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]1([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]([N:20]2[CH2:29][CH2:28][CH:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:30][CH2:31]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 145273-PhenylpentaneHCID 81531DiisopropylethylamineHCID 16228925tert-Butyl 3-amino-4-phenylpiperidine-1-carboxylate

생성물 1

HCID 70197121HCID 70197121, 화합물

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide촉매

실험 절차

To a solution of amine (from Example 104, Step E) and (±) -1, 5-dibromo, 3-phenyl-pentane in 0.5 mL of isobutylnitrile was added 0.080 mL of DIEA and a catalytic amount of tetrabutyl-ammonium iodide. After warming the reaction to 95° C. for 22 h, the mixture was partitioned between 10 mL of CH2Cl2 and 10 mL 1N NaOH. After separating layers, the aqueous phase was extracted with 10 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography eluting with 10% EtOAc in hexanes to provide 10 mg of the title compound: 1H NMR (300 MHz, CDCl3): δ1.2-1.9 (m, 16H), 2.1-2.4 (m, 2H), 2.6-3.0 (m, 6H), 4.0-4.4 (m, 2H), 7.0-7.4 (m, 10H). RF : 0.45 (20% EtOAc in hexanes).

후처리

  1. temperatureAfter warming
  2. customthe reaction to 95° C. for 22 h
  3. customthe mixture was partitioned between 10 mL of CH2Cl2 and 10 mL 1N NaOH
  4. customAfter separating layers
  5. extractionthe aqueous phase was extracted with 10 mL of CH2Cl2
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography
  9. washeluting with 10% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-59274f271fcf4dde9603ab35e27ba74b
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166037

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