Ethyl Acetate → Benzyl 3-(2-amino-1-(6-morpholino-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate

HRID 2361292Notes

Reaction equation

HRID 2361292 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([C:13]2[C:21]3[C:16](=[CH:17][C:18]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][N+:10]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+].CCOC(C)=O>C1COCC1.CO.[Zn]>[NH2:10][CH2:9][CH:8]([C:7]1[C:2]([CH3:1])=[C:3]([NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:4]=[CH:5][CH:6]=1)[C:13]1[C:21]2[C:16](=[CH:17][C:18]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)=[CH:19][CH:20]=2)[NH:15][CH:14]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 67994689Benzyl 2-methyl-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate

Product 1

HCID 67994601Benzyl 3-(2-amino-1-(6-morpholino-1H-indol-3-yl)ethyl)-2-methylphenylcarbamateYield 85%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A heterogeneous solution of benzyl 2-methyl-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate (1.8743 g, 3.64 mmol), ammonium chloride (2.92 g, 54.6 mmol) and zinc (3.57 g, 54.6 mmol) in THF (Ratio: 1.000, Volume: 79 ml) and methanol (Ratio: 1.000, Volume: 79 ml) was stirred under nitrogen for 2.5 hr. EtOAc (60 mL) was added, and the solution was filtered through a pad of CELITE®. The filtrate was concentrated in vacuo; the residue was dissolved in water (50 mL) and EtOAc (75 mL). After separation of the layers, the aqueous layer was extracted with EtOAc (2×75 mL). The organic layers were combined, dried over MgSO4, and concentrated in vacuo to give the desired product (1.4934 g, 3.08 mmol, 85% yield) as a tan solid.

Workup

  1. filtrationthe solution was filtered through a pad of CELITE®
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was dissolved in water (50 mL)
  4. customAfter separation of the layers
  5. extractionthe aqueous layer was extracted with EtOAc (2×75 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5669486885494a14b895dac6bab3556d
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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