Ammonium formate → Ammonium Hydroxide

HRID 975013Notes

Reaction equation

HRID 975013 reaction equation
C([O:8][C:9]([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.C(OC([N:36]1[CH2:41][CH2:40][CH2:39]C[CH:37]1[CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[OH-:8].[NH4+:11].[NH:36]1[CH2:41][CH2:40][CH2:39][CH:37]1[CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1.[NH:11]1[CH2:9][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

8

Reactant 3

HCID 2723923Ammonium formateHCID 120500533-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-1H-indoleHCID 199702443-(N-benzyloxycarbonylpiperid-2-ylmethyl)-1H-indole

Product 3

HCID 14923Ammonium HydroxideHCID 21346Indole, 3-(2-piperidylmethyl)-HCID 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 or the 3-(N-benzyloxycarbonylpiperid-2-ylmethyl)-1H-indole (2.00 mmol), 10% palladium on carbon (0.20 g), and ammonium formate (1.26 g, 20 mmol, 10 eq) in absolute ethanol (15 mL) was stirred under a nitrogen atmosphere for 4 hours. 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 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 or 3-(piperid-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 50 g) and elution with a solution of methylene chloride

Sources & evidence

ORD record
ord-543a21d4a63d49cba553f08fcbb199e1
Source dataset
uspto-grants-1997_03
Patent number
US05607951

Reaction notes

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