Triphenylphosphine → HCID 9850079, compound

HRID 991487Notes

Reaction equation

HRID 991487 reaction equation
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]

Participants

6

Reactant 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

Product 1

HCID 9850079HCID 9850079, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ed7cd55b91cc4393ba3736e2cc2d3a7f
Source dataset
uspto-grants-2002_10
Patent number
US06465481B1

Reaction notes

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