Sodium periodate → HCID 178483658, compound

HRID 1063642Notes

Reaction equation

HRID 1063642 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][OH:18])[CH2:13][CH2:12]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:21].[Na+]>C(Cl)(Cl)(Cl)Cl.O.C(#N)C.O.[Ru](Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:7]([CH3:8])[CH2:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([C:17]([OH:21])=[O:18])[CH2:15][CH2:16]1)=[O:19])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 178483648HCID 178483648, compound

Product 1

HCID 178483658HCID 178483658, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 17.1 g (63.1 mmol) of trans-[2-(4-hydroxymethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester in 60 mL of CCl4, 60 mL of water and 90 mL of acetonitrile were treated with 0.075 g (0.33 mmol, 0.05 eq) of ruthenium (III) chloride-hydrate and 55.4 g (259 mmol, 4.1 eq) of sodium metaperiodate within 30 min. After 6 h the reaction was decanted and washed with CH2Cl2 (×3). The decanted phase was partitioned between CH2Cl2 (×3)/H2O, the organic phase was dried over Na2SO4 and evaporated to yield 17.24 g (96%) of trans-4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexanecarboxylic acid, MS: 284 (M−H−).

Workup

  1. customAfter 6 h the reaction was decanted
  2. washwashed with CH2Cl2 (×3)
  3. customThe decanted phase was partitioned between CH2Cl2 (×3)/H2O
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-064003f714a54824b6ac55c45d0ef589
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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