tert-Butyl 2-[(3R*,4S*)-1-[(2,6-dichlorophenyl)methyl]-3-[(1-hexylpiperidin-4-yl)carbamoyl]-4-methylpyrrolidin-3-yl]acetate → tert-Butyl 2-[(3R*,4S*)-3-[(1-hexylpiperidin-4-yl)carbamoyl]-4-methylpyrrolidin-3-yl]acetate

HRID 446030Notes

Reaction equation

HRID 446030 reaction equation
ClC1C=CC=C(Cl)C=1C[N:10]1[CH2:14][C@@H:13]([CH3:15])[C@@:12]([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])([C:16](=[O:30])[NH:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:19]2)[CH2:11]1>[OH-].[Pd+2].[OH-].CO>[CH2:24]([N:21]1[CH2:20][CH2:19][CH:18]([NH:17][C:16]([C@:12]2([CH2:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[C@H:13]([CH3:15])[CH2:14][NH:10][CH2:11]2)=[O:30])[CH2:23][CH2:22]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 1

HCID 71293842tert-Butyl 2-[(3R*,4S*)-1-[(2,6-dichlorophenyl)methyl]-3-[(1-hexylpiperidin-4-yl)carbamoyl]-4-methylpyrrolidin-3-yl]acetate

Product 1

HCID 71293828tert-Butyl 2-[(3R*,4S*)-3-[(1-hexylpiperidin-4-yl)carbamoyl]-4-methylpyrrolidin-3-yl]acetateYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Methanol (10 ml) and 20% palladium hydroxide (50 mg) were added to 250 mg of tert-butyl 2-[(3R*,4S*)-1-[(2,6-dichlorophenyl)methyl]-3-[(1-hexylpiperidin-4-yl)carbamoyl]-4-methylpyrrolidin-3-yl]acetate obtained in Example 10h, followed by stirring at room temperature for two hours under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated to give the title compound (180 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0805993024fb47208219682df3b1a16c
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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