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

HRID 1857985Notes

Reaction equation

HRID 1857985 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) is shaken under a hydrogen atmosphere (3 atm) for 4 to 24 hours, depending on substrate. The resulting reaction mixture is filtered through diatomaceous earth, and the filtrate is evaporated under reduced pressure. The residue is column chromatographed using silica gel (approximately 50 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. filtrationis filtered through diatomaceous earth
  3. customthe filtrate is evaporated under reduced pressure
  4. customchromatographed
  5. washsilica gel (approximately 50 g) and elution with a solution of methylene chloride

Sources & evidence

ORD record
ord-f322a42982f649cca0d0fbf0ab0d0f49
Source dataset
uspto-grants-2000_11
Patent number
US06150388

Reaction notes

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