Cyclopentanecarboxylic acid → HCID 66985078, compound

HRID 1616675Notes

Reaction equation

HRID 1616675 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[CH:47]1([C:52]([OH:54])=O)[CH2:51][CH2:50][CH2:49][CH2:48]1.C(N(C(C)C)C(C)C)C.[CH3:64][O:65][C:66]1[C:71]2[CH2:72][C@@H:73]3[C:78]([CH3:80])([CH3:79])[C@:77]([CH3:81])([C:70]=2[CH:69]=[CH:68][CH:67]=1)[CH2:76][CH2:75][NH:74]3>CN(C)C=O.C(OCC)(=O)C>[CH:47]1([C:52]([N:74]2[CH2:75][CH2:76][C@:77]3([CH3:81])[C:78]([CH3:80])([CH3:79])[C@H:73]2[CH2:72][C:71]2[C:66]([O:65][CH3:64])=[CH:67][CH:68]=[CH:69][C:70]=23)=[O:54])[CH2:48][CH2:49][CH2:50][CH2:51]1

Participants

8

Reactant 5

HCID 18840Cyclopentanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10966789HCID 10966789, compound

Product 1

HCID 66985078HCID 66985078, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.27 g; alternatively N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate may be used) is added to a solution of cyclopentanecarboxylic acid (100 mg) and ethyldiisopropylamine (0.2 mL) in N,N-dimethylformamide (10 mL). The resulting solution is stirred at ambient temperature for 15 min before (2R,6S)-10-methoxy-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine (0.20 g) is added. After stirring the solution overnight, ethyl acetate is added and the resulting mixture is washed with aqueous Na2CO3 solution and dried (Na2SO4). After evaporation of the solvent under reduced pressure, the product is obtained as a yellow oil.

Workup

  1. additionis added
  2. additionis added
  3. washthe resulting mixture is washed with aqueous Na2CO3 solution
  4. dry with materialdried (Na2SO4)
  5. customAfter evaporation of the solvent under reduced pressure
  6. customthe product is obtained as a yellow oil

Sources & evidence

ORD record
ord-670fb3225cb741ad97234c04c1b7fa47
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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