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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
ノート
印刷プレビュー

反応式

HRID 991487 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed7cd55b91cc4393ba3736e2cc2d3a7f
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06465481B1

反応ノート

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