1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18001111, 화합물

HRID 969276노트

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HRID 969276 반응식
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[N+:14]([O-])=O)=O.N12CCCN=C1CCCCC2.C1C=CC([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:35][C:36]2[CH:41]=[C:40]([C:42]#[N:43])[CH:39]=[CH:38][CH:37]=2)=CC=1.[Br-]>C1(C)C=CC=CC=1>[NH2:14][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:3]=1[CH2:1][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]([C:42]#[N:43])[CH:41]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2778355(3-Cyanobenzyl)triphenylphosphonium bromideHCID 18001104Ethyl 4-formyl-3-nitrobenzoate

생성물 1

HCID 18001111HCID 18001111, 화합물수율 136%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

Ethyl 4-formyl-3-nitrobenzoate (5.81 g) was dissolved in 70 ml of toluene, then 2.1 ml of 1,8-diazabicyclo[5.4.0]-undec-7-ene and the mixture was stirred at 80° C. for one hour. To the reaction solution, 2.69 g of 3-[(1,1,1-triphenylphosphonio)methyl]benzonitrile bromide was added, and the mixture was stirred at 80° C. for 24 hours. Insoluble matters were filtered out and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1) as an eluting solvent. The resulting intermediate (3.1 g) was dissolved in a mixed solvent of 50 ml of ethanol and 10 ml of tetrahydrofuran, then 1 g of a palladium oxide-barium sulfate complex was added and the mixture was stirred in a hydrogen atmosphere at room temperature for 3 days. The reaction solution was filtered through Celite and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (2:1) as an eluting solvent to give 2.35 g of ethyl 3-amino-4-[2-(3-cyanophenyl)ethyl]benzoate.

후처리

  1. filtrationInsoluble matters were filtered out
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was purified by silica gel column chromatography
  4. dissolutionThe resulting intermediate (3.1 g) was dissolved in a mixed solvent of 50 ml of ethanol and 10 ml of tetrahydrofuran
  5. addition1 g of a palladium oxide-barium sulfate complex was added
  6. stirringthe mixture was stirred in a hydrogen atmosphere at room temperature for 3 days
  7. filtrationThe reaction solution was filtered through Celite
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b31f77fc53c9453585b6d15f3bcbf7a8
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307074B2

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