Water → HCID 178483642, compound

HRID 1063649Notes

Reaction equation

HRID 1063649 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH3:19])[CH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][CH:17]=[O:18])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C(#N)C.O.I([O-])(=O)(=O)=[O:26].[Na+]>C(Cl)(Cl)(Cl)Cl.[Ru](Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:7]([CH3:19])[CH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][C:17]([OH:26])=[O:18])[CH2:12][CH2:11]1)=[O:20])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 178483639HCID 178483639, compound

Product 1

HCID 178483642HCID 178483642, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

0.66 g (2.3 mmol) of trans-methyl-{2-[4-(2-oxo-ethyl)-cyclohexyl]-ethyl}-carbamic acid tert-butyl ester were dissolved in 2 mL of CCl4, 2 mL of acetonitrile and 3 mL of water. To this mixture were added 2.4 mg (0.012 mmol, 0.01 eq) of anhydrous ruthenium (III) chloride, followed by 2.04 g (9.5 mmol, 4.1 eq) of sodium metaperiodate in small portions. Stirring was continued at RT for 2 h, the mixture was filtered and partitioned between CH2Cl2 and water. The organic phase was washed with water and dried over magnesium sulfate. Column chromatography of the crude product with a gradient of n-heptane: EtOAc 1:4 to 1:1 gave 430 mg (62%) of trans-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-acetic acid as colorless oil, MS: 317 (M+NH4+).

Workup

  1. filtrationthe mixture was filtered
  2. custompartitioned between CH2Cl2 and water
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-50e2c9eec1604330827a0fe23716df92
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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