Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate → (+/-)Methyl 4-[5-(2-cyclopentylacetamido)-1-ethyl-2,3-dihydroindol-3-ylmethyl]-3-methoxybenzoate

HRID 275144Notes

Reaction equation

HRID 275144 reaction equation
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH3:20])[CH:14]=[C:13]3[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)=O>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH3:20])[CH2:14][CH:13]3[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 14626833Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate

Product 1

HCID 14626834(+/-)Methyl 4-[5-(2-cyclopentylacetamido)-1-ethyl-2,3-dihydroindol-3-ylmethyl]-3-methoxybenzoateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Palladium-on-carbon (10% w/w, 0.5 g.) was added to a mixture of methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate (0.5 g., prepared as described in Example 80), and formic acid (99%, 20 ml.), under an atmosphere of nitrogen. The mixture was vigorously stirred and heated at 80° C. for one hour. The cooled mixture was filtered through a pad of diatomaceous earth, the filter cake washed with methanol, and the filtrate evaporated. The resulting oil was dissolved in ethyl acetate (30 ml.) washed with water, brine, then dried (MgSO4) and evaporated. The product was purified by flash chromatography on silica gel (4 cm. diameter column), eluting with 2:3 v/v ethyl acetate:hexane, to give the title compound (0.37 g., 80%) as a foam; NMR (250 MHz, DMSO-d6): 1.04(t,3H, --CH2CH3); 1.15(m,2H, cyclopentyl ring); 1.4-1.8(m,6H, cyclopentyl ring); 2.2(m,3H); 2.7(dd,1H); 2.85-3.2(m,5H); 3.45(m,1H); 3.86(s,3H, OCH3); 3.87(s,3H, OCH3); 6.43(d,1H); 7.20 (m,2H); 7.30(d,1H); 7.50(m,2H); 9.47(s,1H, NH).

Workup

  1. filtrationThe cooled mixture was filtered through a pad of diatomaceous earth
  2. washthe filter cake washed with methanol
  3. customthe filtrate evaporated
  4. dissolutionThe resulting oil was dissolved in ethyl acetate (30 ml.)
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe product was purified by flash chromatography on silica gel (4 cm. diameter column)
  9. washeluting with 2:3 v/v ethyl acetate

Sources & evidence

ORD record
ord-ba260941d05447ec8f3738b7f069d3a1
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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