3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-1H-indole → Ammonium Hydroxide

HRID 862172Notes

Reaction equation

HRID 862172 reaction equation
C([O:8]C([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1>[Pd].C(O)C>[OH-:8].[NH4+:11].[NH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1

Participants

5

Reactant 1

HCID 120500533-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-1H-indole

Product 2

HCID 14923Ammonium HydroxideHCID 185089963-(pyrrolidin-2-ylmethyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the 3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-1H-indole (2.00 mmol) and 10% palladium on carbon (0.20 g) in absolute ethanol (15 mL) was shaken under a hydrogen atmosphere (3 atm) for 4-24 hours, depending on substrate. The resulting reaction mixture was filtered through diatomaceous earth, and the filtrate was evaporated under reduced pressure. The residue was column chromatographed using silica gel (approximately 10 g) and elution with a solution of methylene chloride: methanol: ammonium hydroxide [8:2:0.2] or other appropriate solvent system to afford the corresponding 3-(pyrrolidin-2-ylmethyl)-1H-indole.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through diatomaceous earth
  3. customthe filtrate was evaporated under reduced pressure
  4. customchromatographed
  5. washsilica gel (approximately 10 g) and elution with a solution of methylene chloride

Sources & evidence

ORD record
ord-98ff231d012445cf80d0239de09e7d99
Source dataset
uspto-grants-1998_02
Patent number
US05717102

Reaction notes

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