Ammonium Acetate → benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)propyl)-2-methylphenylcarbamate

HRID 2361394Notes

Reaction equation

HRID 2361394 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH:15]([C:21]3[C:22]([CH3:38])=[C:23]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:24]=[CH:25][CH:26]=3)[CH:16]([N+:18]([O-])=O)[CH3:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1.C([O-])(=O)C.[NH4+]>CO.O1CCCC1.CCOC(C)=O.[Zn]>[NH2:18][CH:16]([CH3:17])[CH:15]([C:21]1[C:22]([CH3:38])=[C:23]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=[CH:25][CH:26]=1)[C:10]1[C:9]2[C:13](=[CH:14][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=2)[NH:12][CH:11]=1

Participants

7

Reactant 2

HCID 517165Ammonium AcetateHCID 67994587benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate

Product 1

HCID 67994898benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)propyl)-2-methylphenylcarbamateYield 92%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitropropyl)-2-methylphenylcarbamate (1.6194 g, 3.13 mmol), ammonium acetate (2.51 g, 46.9 mmol) and zinc (3.07 g, 46.9 mmol) in methanol (Ratio: 1.000, Volume: 57.9 ml) and tetrahydrofuran (Ratio: 1.000, Volume: 57.9 ml) was stirred under nitrogen. After 5 h, the reaction was diluted with EtOAc and filtered through a wad of CELITE®. The filtrate was concentrated in vacuo, and the residue was dissolved in EtOAc (75 mL) and saturated aqueous NaHCO3 (30 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (2×75 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo to give benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)propyl)-2-methylphenylcarbamate (1.3975 g, 2.87 mmol, 92% yield, mixture of 2 isomers) as a colorless oil, LC/MS (M+H)=488.30, 488.30.

Workup

  1. filtrationfiltered through a wad of CELITE®
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (75 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×75 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea51650a1a7d43d980df1f13d05ebe07
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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