Methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]-indolyl}propanoate → Methyl 3-[5-(aminopropoxy)indolyl]propanoate

HRID 1295123Notes

Reaction equation

HRID 1295123 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:19]2)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:19]2

Participants

4

Reactant 1

HCID 22570338Methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]-indolyl}propanoate

Product 1

HCID 66819503Methyl 3-[5-(aminopropoxy)indolyl]propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]indolyl}propanoate (300 mg, 0.73 mmol), as prepared in the preceding step, 10% palladium(0) on carbon (50 mg) in ethanol (20 mL) was stirred at ambient temperature under hydrogen (balloon) for 3 h. The catalyst was removed by filtration through Celite. The filtrate was concentrated to give the title compound as an off white solid (150 mg, 74%). 1H-NMR (400 MHz, CDCl3/CD3OD) δ 7.25 (d, J=8.9 Hz, 1H), 7.13 (d, J=2.6 Hz, 1H), 7.08 (d, J=2.5 Hz, 1H), 6.85 (dd, J=8.9, 2.5 Hz, 1H), 6.38 (d, J=2.9 Hz, 1H), 4.43 (t, J=6.8 Hz, 2H), 4.10 (t, J=5.8 Hz, 2H), 3.66 (s, 3H), 3.01 (q, J=7.0 Hz, 2H), 2.83 (t, J=6.8 Hz, 2H), 2.04 (m, 2H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d989f579e6164c1aa0a8ed0ca72ac994
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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