Ethanol → HCID 18706904, compound

HRID 1422085Notes

Reaction equation

HRID 1422085 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:8]([O:15][C:16]1[C:17]2[N:18]3[C:22](=[CH:23][CH:24]=1)[C:21]([CH2:25][CH3:26])=[C:20]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:29][CH:28]=1)[C:19]3=[C:41]([CH2:43][O:44][CH2:45][CH2:46][CH2:47][CH2:48]Cl)[CH:42]=2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)C>CN(C)C=O.O.C(OCC)(=O)C>[CH2:8]([O:15][C:16]1[C:17]2[N:18]3[C:22](=[CH:23][CH:24]=1)[C:21]([CH2:25][CH3:26])=[C:20]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:29][CH:28]=1)[C:19]3=[C:41]([CH2:43][O:44][CH2:45][CH2:46][CH2:47][CH2:48][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:42]=2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 187069385-Benzyloxy-2-(4-benzyloxyphenyl)-3-((4-chlorobutoxy)methyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

Product 1

HCID 18706904HCID 18706904, compoundYield 12.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyrrolidine (66 mg, 0.93 mmol) was dissolved in 50 ml of dry dimethylformamide under a nitrogen atmosphere and sodium hydride (60% in oil) (36 mg, 0.89 mmol) was added. The mixture was stirred for 1/2 hour. 5Benzyloxy-2-(4-benzyloxyphenyl)-3-((4-chlorobutoxy)methyl)-1-ethylpyrrolo[2,1,5-cd]indolizine (0.256 g, 0.443 mmol) was added and the mixture was stirred at 55-65° for 6 days. Ethanol (10 ml) was added dropwise, and the reaction mixture was diluted with 250 ml of water. The organic material was extacted into ethyl acetate (4×100 ml), and the combined oranic layers were washed with brine and dried over sodium solfate. The solvent was evaporated and the crude product was purified by column chromatography over silica gel 60, using 6% of methanol in dichloromethane as the eluent. Fractions containing the product were collected to afford 34 mg (12%) of 5-benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-3-((4-pyrrolidinobutoxy)methyl)pyrrolo[2,1,5-cd ]indolizine as an oil. MS(FAB): m/z613 (M+1). 1H-NMR (DMSO-d6, 300 MHz) δ: 1.27-1.49 (m, 11H); 2.50-2.56 (m, 6H); 3.05 (q, 2H); 3.40 (t, 2H); 4.71 (s, 2H); 5.20 (s, 2H); 5.58 (s, 2H); 7.20 (d, 2H); 7.31-7.64 (m, 14H); 7.95 (d, 1H).

Workup

  1. stirringthe mixture was stirred at 55-65° for 6 days
  2. washthe combined oranic layers were washed with brine
  3. dry with materialdried over sodium solfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by column chromatography over silica gel 60
  6. additionFractions containing the product
  7. customwere collected

Sources & evidence

ORD record
ord-c54c39e496014976bd7cc32c08cf4436
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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