Water → (3R,4S)-4-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-piperidine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

HRID 658234Notes

Reaction equation

HRID 658234 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[Cl:29])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:6]1)=[O:4].C[O-].[Na+].O>CO>[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[Cl:29])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 671487224-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

Product 1

HCID 67148356(3R,4S)-4-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-piperidine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a sol. of compound 4-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (0.21 g, 0.38 mmol) in MeOH (2 mL) under Ar was added NaOMe (6 mg, 0.11 mmol). The mixture was stirred for 3 days at 70° C. Water was added, and the mixture was extracted with EtOAc. The org. phase was washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The title compound (150 mg, 72%) was not further purified. LC-MS: tR=1.18 min, ES+=538.32.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washphase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-d3d8426da7554bdfa1b042f21057a997
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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