Water → (3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-3-carboxylic acid

HRID 658235Notes

Reaction equation

HRID 658235 reaction equation
C[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].[OH-].[Na+].O>CO>[C:33]([O:32][C:30]([N:7]1[CH2:8][CH2:9][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)[C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 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

Product 1

HCID 59234216(3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-3-carboxylic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a sol. of compound (rac.)-(3R*,4S*)-4-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (0.15 g, 0.27 mmol) in MeOH (1 mL) was added aq. 1M NaOH (1 mL). The mixture was stirred at 70° C. for 2 h. 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 crude residue was purified on a pad of silica gel to yield the title compound (93 mg, 65%). LC-MS: tR=1.12 min, ES+=524.24.

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
  6. customThe crude residue was purified on a pad of silica gel

Sources & evidence

ORD record
ord-df4a4e1d4b474cfc818b9a86b3dbab42
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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