Lithium Chloride → 4-[5-Acetyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

HRID 32207Notes

Reaction equation

HRID 32207 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18](OS(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)(=O)=O)[CH:17]=[CH:16][C:15]=2[CH:37]2[CH2:42][C:41]([CH3:44])([CH3:43])[CH2:40][C:39]([CH3:46])([CH3:45])[CH2:38]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:52]([O:54]CC)=[CH2:53])CCC.[Cl-].[Li+].C(=O)([O-])O.[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[C:18]([C:52](=[O:54])[CH3:53])[CH:17]=[CH:16][C:15]=2[CH:37]2[CH2:38][C:39]([CH3:46])([CH3:45])[CH2:40][C:41]([CH3:43])([CH3:44])[CH2:42]2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 597694204-[5-(Nonafluorobutane-1-sulfonyloxy)-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 597694454-[5-Acetyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl esterYield 96.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-[5-(nonafluorobutane-1-sulfonyloxy)-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester (267 mg, 0.382 mmol) produced in Example (81c), tributyl(1-ethoxyvinyl)tin (0.16 mL, 0.458 mmol), dichlorobis(triphenylphosphine)palladium(II) (41 mg, 0.0573 mmol), lithium chloride (48.6 mg, 1.15 mmol) and dimethylformamide (3 mL) was stirred for 6 hours and 10 minutes at an external temperature of 90° C. under a nitrogen atmosphere. Saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were then added to the reaction mixture. The mixture was filtered through Celite, and the resultant filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 163 mg of the title compound as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe resultant filtrate was concentrated under reduced pressure
  3. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-013805a1400b46e4b790f765856e4f1b
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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