4-[3-(2-Ethoxycarbonyl-2-oxo-ethyl)-4-nitro-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester → 5-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 19892Notes

Reaction equation

HRID 19892 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([CH2:24][C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=O)[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[CH2:30]([O:29][C:27]([C:25]1[NH:21][C:18]2[C:17]([CH:24]=1)=[CH:16][C:15]([O:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:13][CH2:12]1)=[CH:20][CH:19]=2)=[O:28])[CH3:31]

Participants

4

Reactant 1

HCID 670179194-[3-(2-Ethoxycarbonyl-2-oxo-ethyl)-4-nitro-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 441849005-(1-tert-Butoxycarbonyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[3-(2-ethoxycarbonyl-2-oxo-ethyl)-4-nitro-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (example 43, step 2, 42.25 g, 1.0 eq.), palladium on activated charcoal (10%, 2.111 g, 0.02 eq.) in ethanol (950 mL) was hydrogenated at 30° C. for 9 h. The mixture was filtered, washed with ethanol and evaporated to dryness. The product was recrystallized from ethyl acetate and heptane to yield 25.998 g (69%) as white crystals. MS (m/e): 388.2 (M, 45%).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with ethanol
  3. customevaporated to dryness
  4. customThe product was recrystallized from ethyl acetate and heptane
  5. customto yield 25.998 g (69%) as white crystals

Sources & evidence

ORD record
ord-37ce066644b14e2498f1eddf831c381f
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Reaction notes

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