(R)-benzyl-2-(5-(2-(phenylsulfonyl)ethyl)-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate → (R)-(1-methylpyrrolidin-2-yl)(5-(2-(phenylsulfonyl)ethyl)-1H-indol-3-yl)methanone

HRID 473058Notes

Reaction equation

HRID 473058 reaction equation
C(O[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][CH2:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:25]=2)[NH:20][CH:19]=1)=[O:17])=O)C1C=CC=CC=1>CC(C)=O.CS(O)(=O)=O.C=O.[Pd]>[CH3:9][N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][CH2:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:30])=[O:31])[CH:25]=2)[NH:20][CH:19]=1)=[O:17]

Participants

6

Reactant 1

HCID 46195789(R)-benzyl-2-(5-(2-(phenylsulfonyl)ethyl)-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate

Product 1

HCID 9908745(R)-(1-methylpyrrolidin-2-yl)(5-(2-(phenylsulfonyl)ethyl)-1H-indol-3-yl)methanoneYield 65%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 712FormaldehydeSolventHCID 6395Methanesulfonic AcidSolventHCID 23938PalladiumSolvent

Procedure

A suspension of (R)-benzyl-2-(5-(2-(phenylsulfonyl)ethyl)-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate (5.0 g) in 50 ml acetone, methanesulfonic acid, formaldehyde and 10% Pd/C was subject to hydrogenation at 45 psi. Upon completion of the reaction the catalyst was filtered off and the solvent removed under vacuum to provide the title compound in about 65-75% yield. Mass (M+Na) 419.5

Workup

  1. customUpon completion of the reaction the catalyst
  2. filtrationwas filtered off
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-32d904fee3e54f058e09eed99808ceb3
Source dataset
uspto-grants-2014_01
Patent number
US08633239B2

Reaction notes

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