HCID 70873632, compound → HCID 70873421, compound

HRID 2172231Notes

Reaction equation

HRID 2172231 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:34])([CH3:33])[CH2:23][CH2:24][O:25]CC3C=CC=CC=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:34])([CH3:33])[CH2:23][CH2:24][OH:25])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 70873632HCID 70873632, compound

Product 1

HCID 70873421HCID 70873421, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

4-[4-(4-Benzyloxy-2-hydroxy-2-methylbutoxy)phenyl]piperazine-1-carboxylic acid tert-butyl ester (6.16 g, 13.1 mmol), palladium hydroxide on carbon (0.62 g) and ethanol (62 ml) were mixed and stirred at 50 to 60° C. under a hydrogen atmosphere for 9 hours. The mixture was filtered through Celite to remove the catalyst, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100) to afford the title compound as a colorless powder (3.75 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100)

Sources & evidence

ORD record
ord-18ecd697fe774a3cb4290ecae7a1d138
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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