Water → 1'-(3-Methoxy-4-nitro-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl ester

HRID 604290Notes

Reaction equation

HRID 604290 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O.[C:25](=[O:28])([O-])[OH:26].[Na+]>C(#N)C.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[C:15]([O:26][C:25]([N:21]1[CH2:22][CH2:23][CH:18]([CH:15]2[CH2:16][CH2:17][N:12]([C:5]3[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:13][CH2:14]2)[CH2:19][CH2:20]1)=[O:28])([CH3:18])([CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 598602801-(3-Methoxy-4-nitro-phenyl)-[4,4']bipiperidine

Product 1

HCID 598602671'-(3-Methoxy-4-nitro-phenyl)-[4,4']bipiperidinyl-1-carboxylic acid tert-butyl esterYield 92%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1-(3-methoxy-4-nitro-phenyl)-[4,4′]bipiperidinyl (1.75 g, 5.48 mmol), di-tert-butyl-dicarboxylate (1.20 g, 5.48 mmol) in acetonitrile (55 mL), zirconium tetrachloride (128 mg, 0.55 mmol) is added and the mixture is stirred at ambient temperature for 30 min. After water and aqueous sodium hydrogen carbonate are added, the mixture is filtrated and dried to give 1′-(3-Methoxy-4-nitro-phenyl)-[4,4′]bipiperidinyl-1-carboxylic acid tert-butyl ester (5.11 g, 92% yield) as yellow solids.

Workup

  1. additionis added
  2. filtrationthe mixture is filtrated
  3. customdried

Sources & evidence

ORD record
ord-565f3da2c21542e089aec63f1b55bf21
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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