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Triphenylphosphine → Tert-butyl 7-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 991487
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HRID 991487 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH3:38][O:39][C:40]1[CH:41]=[C:42]([OH:48])[CH:43]=[CH:44][C:45]=1[O:46][CH3:47].[C:49]([C:51]1[CH:56]=[CH:55][C:54]([CH:57](O)[CH2:58][CH2:59][CH2:60][N:61]2[CH2:68][CH:67]3[CH2:69][CH:63]([CH2:64][N:65]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:66]3)[CH2:62]2)=[CH:53][CH:52]=1)#[N:50]>C(Cl)Cl>[C:49]([C:51]1[CH:52]=[CH:53][C:54]([CH:57]([O:48][C:42]2[CH:43]=[CH:44][C:45]([O:46][CH3:47])=[C:40]([O:39][CH3:38])[CH:41]=2)[CH2:58][CH2:59][CH2:60][N:61]2[CH2:62][CH:63]3[CH2:69][CH:67]([CH2:66][N:65]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:64]3)[CH2:68]2)=[CH:55][CH:56]=1)#[N:50]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 162513,4-DimethoxyphenolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11338532Tert-butyl 7-[4-(4-cyanophenyl)-4-hydroxybutyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

생성물 1

HCID 9850079Tert-butyl 7-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Triphenylphosphine (1.11 g; 4.25 mmol) in 5 mL CH2Cl2 and 1,1′-(azodicarbonyl)dipiperidine (1.07 g; 4.25 mmol) in 15 mL CH2Cl2 were added to a stirred solution of 3,4-dimethoxyphenol (0.65 g; 4.25 mmol) and tert-butyl 7-[4-(4-cyanophenyl)-4-hydroxybutyl]-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylate (from step (x) above; 0.85 g; 2.12 mmol). After 3 h, the precipitate was filtered off, and the filtrate concentrated. The residue was dissolved in aqueous tartaric acid (1 M; 25 mL) and the solution was washed with diethyl ether. The aqueous phase was made basic with and extracted again with diethyl ether. The organic layer from this second extraction was separated, dried (Na2SO4) and then concentrated to give the title compound in 21% yield.

후처리

  1. filtrationthe precipitate was filtered off
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue was dissolved in aqueous tartaric acid (1 M; 25 mL)
  4. washthe solution was washed with diethyl ether
  5. extractionextracted again with diethyl ether
  6. extractionThe organic layer from this second extraction
  7. customwas separated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ed7cd55b91cc4393ba3736e2cc2d3a7f
출처 데이터셋
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06465481B1

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