Benzylamine → 4-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1267117노트

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HRID 1267117 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:28][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 3

HCID 7504BenzylamineHCID 23676156Sodium t-butoxideHCID 54371851Tert-butyl 4-(4-bromophenyl)-3,6-dihydropyridine-1(2h)-carboxylate

생성물 1

HCID 537487374-(4-Benzylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester수율 73.7%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a solution of 4-(4-bromo-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.34 g), benzylamine (0.12 g) and sodium tert-butoxide (0.13 g) in toluene (8 mL) were added tris(dibenzylidene acetone)dipalladium (2.2 mg) and Binap (4.6 mg) and the mixture was heated at 80° C. for 16 hours. The solution was then cooled to room temperature, filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography eluting with petroleum ether/AcOEt (90/10) and the oily residue was crystallized from diisopropyl ether to give the title compound (0.27 g) as white crystals.

후처리

  1. temperatureThe solution was then cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography
  5. washeluting with petroleum ether/AcOEt (90/10)
  6. customthe oily residue was crystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-9c1ca8c990864d51a54fac36ad021f03
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552022B1

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