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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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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 991487
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]
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Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ed7cd55b91cc4393ba3736e2cc2d3a7f
Quelldatensatz
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06465481B1

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