HCID 54249514, compound → HCID 54432397, compound

HRID 2271003Notes

Reaction equation

HRID 2271003 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:13]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:12][N:11]1[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)(=[O:29])=[O:28])C1C=CC=CC=1>CO.[H][H].[OH-].[OH-].[Pd+2]>[C:19]([O:18][C:16]([N:14]1[C@H:13]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:12][N:11]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C@@H:10]([CH2:9][OH:8])[CH2:15]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 1

HCID 54249514HCID 54249514, compound

Product 1

HCID 54432397HCID 54432397, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Palladium hydroxide on carbon (700 mg) was added to a solution of (2R,5R)-2-benzyloxymethyl-4-(tert-butoxycarbonyl)-1-(4-methoxybenzenesulfonyl)-5-(2-methylpropyl)piperazine (6.4 g) in MeOH (60 ml), and the mixture was hydrogenated in hydrogen at 3.5 atm for 4 hours at ambient temperature. The catalyst was removed by filtration through a celite pad and the filtrate was washed with MeOH. The filtrate and combined washings were concentrated in vacuo to give 5.3 g of (2R,5R)-4-(tert-butoxycarbonyl)-2-hydroxymethyl-1-(4-methoxybenzenesulfonyl)-5-(2-methylpropyl)piperazine as white crystals.

Workup

  1. customThe catalyst was removed by filtration through a celite pad
  2. washthe filtrate was washed with MeOH
  3. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-555ef81a9d46492f80a84c10c88a56e0
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

Loading…