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Ethyl Acetate → (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 2428192
Notes
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Reaction equation

HRID 2428192 reaction equation
CO[Na].[CH3:4][O:5][C:6]([CH:8]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[CH2:12][CH2:11][N:10]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:9]1)=[O:7].CCOC(C)=O>CO>[CH3:4][O:5][C:6]([C@@H:8]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[CH2:12][CH2:11][N:10]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:9]1)=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 671487224-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl esterHCID 178418582HCID 178418582, compound2×

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 EsterYield 47.3%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

MeONa (2.27 g, 42 mmol) was added to a sol. of compounds D5 (22.6 g, 42 mmol) in MeOH (200 mL). The mixture was stirred at 70° C. for 6 h, and MeONa (2.27 g, 42 mmol) was added again. The mixture was stirred at 70° C. for 2 days, and was allowed to cool to rt. EtOAc was added, and the resulting mixture was washed with aq. 1M HCl and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 5:95→10:90) yielded the title compound (10.7 g, 47%). LC-MS: tR=1.19 min, ES+=538.39.

Workup

  1. stirringThe mixture was stirred at 70° C. for 2 days
  2. temperatureto cool to rt
  3. washthe resulting mixture was washed with aq. 1M HCl and brine
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC (MeOH/CH2Cl2 5:95→10:90)

Sources & evidence

ORD record
ord-bd4d4809daea4306a7e37d0ee08b8df4
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968720B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes