Ethanol → HCID 44215053, compound

HRID 1532365Notes

Reaction equation

HRID 1532365 reaction equation
C(OC(=O)[N:10]([CH2:21][CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([CH3:43])([CH3:42])[C:33]([N:35]3[CH:39]4[CH2:40][CH2:41][CH:36]3[CH2:37][CH2:38]4)=[O:34])[CH:30]=2)[NH:25][C:24]=1[C:44]1[CH:49]=[C:48]([CH3:50])[CH:47]=[C:46]([CH3:51])[CH:45]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)C1C=CC=CC=1.C(O)C.C(OCC)(=O)C.[H][H]>[Pd].C(Cl)Cl.CO>[CH:36]12[N:35]([C:33](=[O:34])[C:32]([C:29]3[CH:30]=[C:31]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24]([C:44]3[CH:45]=[C:46]([CH3:51])[CH:47]=[C:48]([CH3:50])[CH:49]=3)=[C:23]4[CH2:22][CH2:21][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)([CH3:43])[CH3:42])[CH:39]([CH2:38][CH2:37]1)[CH2:40][CH2:41]2

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 69951628HCID 69951628, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44215053HCID 44215053, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 80.2 mg (0.115 mmol) of [2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-[4-(pyridin-3yl)butyl]carbamic acid benzyl ester, 40 mg of 10% palladium on carbon, 4 mL of absolute ethanol, and 4 mL of ethyl acetate was shaken with hydrogen (46 psig) in a pressure vessel for 6 hours. The catalyst was removed by filtration through Celite under nitrogen, and the filtrate was concentrated in vacuo at room temperature. The residue was purified by preparative TLC on 4 Analtech tapered silica gel plates (20×20 cm), which were developed in 92.5:7.5:0.75 CH2Cl2-MeOH-concentrated NH4OH. The product band from each plate was isolated, combined, and extracted with 92.5:7.5:0.75 CH2C12-MeOH-concentrated NH4OH. Concentration of the extracts in vacuo yielded 53.8 mg (81%) of a pale yellow, stiff gum or glass; essentially homogeneous by TLC in 92.5:7.5:0.75 CH2Cl2-MeOH-concentrated MeOH-concentrated NH4OH. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (ESI): m/e=563.5 (M+H).

Workup

  1. customThe catalyst was removed by filtration through Celite under nitrogen
  2. concentrationthe filtrate was concentrated in vacuo at room temperature
  3. customThe residue was purified by preparative TLC on 4 Analtech tapered silica gel plates (20×20 cm), which
  4. customThe product band from each plate was isolated
  5. extractionextracted with 92.5:7.5:0.75 CH2C12-MeOH-concentrated NH4OH
  6. customConcentration of the extracts in vacuo yielded 53.8 mg (81%) of a pale yellow, stiff gum or glass

Sources & evidence

ORD record
ord-69241aba780545c1aca03251bbc06db1
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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