tert-Butyl 4-[(3R*,4S*)-1-benzyl-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate → tert-Butyl 4-[(3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate

HRID 446006Notes

Reaction equation

HRID 446006 reaction equation
C([N:8]1[CH2:12][C@@H:11]([CH3:13])[C@@:10]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[O:15])[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[C:34]([O:33][C:31](=[O:32])[CH2:30][C@@:10]1([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[O:15])[C@H:11]([CH3:13])[CH2:12][NH:8][CH2:9]1)([CH3:37])([CH3:35])[CH3:36]

Participants

4

Reactant 1

HCID 71293658tert-Butyl 4-[(3R*,4S*)-1-benzyl-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate

Product 1

HCID 71293654tert-Butyl 4-[(3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylateYield 94.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

20% palladium hydroxide (724 mg) was added to a solution of tert-butyl 4-[(3R*,4S*)-1-benzyl-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate obtained in Example 3a (1.33 g, 2.58 mmol) in methanol (30 ml), which was stirred under a hydrogen atmosphere overnight. The reaction liquid was filtered and concentrated under reduced pressure to give the title compound (1.04 g, yield: 94.7%).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-087e41c0250342f5a584105c7fc92afd
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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