t-Butyl 2-(5-ethoxycarbonyl-2-methoxymethoxy-phenyl)-pyrrole-1-carboxylate → t-Butyl 2-(5-ethoxycarbonyl-2-methoxymethoxy-phenyl)-pyrrolidine-1-carboxylate

HRID 13261Notes

Reaction equation

HRID 13261 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:24][CH2:25][O:26][CH3:27])=[C:10]([C:12]2[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH:11]=1)=[O:5])[CH3:2].[H][H]>[Pt].[C].C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:24][CH2:25][O:26][CH3:27])=[C:10]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 23145511t-Butyl 2-(5-ethoxycarbonyl-2-methoxymethoxy-phenyl)-pyrrole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 23145317t-Butyl 2-(5-ethoxycarbonyl-2-methoxymethoxy-phenyl)-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 702EthanolSolvent

Procedure

8.2 g of 5% platinum-carbon catalyst was added to an ethanol (400 ml) solution of 28.4 g of t-butyl 2-(5-ethoxycarbonyl-2-methoxymethoxy-phenyl)-pyrrole-1-carboxylate, and the reaction liquid was stirred for 3 days in a hydrogen atmosphere. The catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/6.5 to 1/6) to obtain the entitled compound as a colorless oily substance.

Workup

  1. customthe reaction liquid
  2. customThe catalyst was removed through filtration through Celite
  3. customthe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/6.5 to 1/6)
  5. customto obtain the entitled compound as a colorless oily substance

Sources & evidence

ORD record
ord-e564ff659c6b4653a27f93c8c3cc34d7
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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