Acetonitrile → HCID 66731917, compound

HRID 1963118Notes

Reaction equation

HRID 1963118 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([CH2:16][OH:17])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH3:21])=[O:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:25].[Na+].C(#N)C>C(Cl)(Cl)(Cl)Cl.O.C(Cl)Cl.[Ru](Cl)(Cl)Cl>[C:1]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([C:16]([OH:25])=[O:17])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH3:21])=[O:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 66731624HCID 66731624, compound

Product 1

HCID 66731917HCID 66731917, compoundYield 99.1%

Reagents, catalysts & solvents 4

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(4-tert-butylbenzyl)-4-(hydroxymethyl)piperidine-1-carboxylate (2.9 g, 9.08 mmol) in carbon tetrachloride (18 mL) was added sodium periodate (5.83 g, 27.24 mmol) and water (27 mL). Acetonitrile (18 mL) was added to this mixture, followed by ruthenium(III) chloride (0.041 g, 0.20 mmol). The resulting biphasic mixture was stirred vigorously at room temperature for 2 h. The reaction mixture was diluted with water and DCM, the aqueous layer was extracted with DCM (×3). The combined organic layers were dried over MgSO4 and evaporated to give the product as an oil (3.0 g, 98%) MS m/z 332 (M−H)−.

Workup

  1. extractionthe aqueous layer was extracted with DCM (×3)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-b14b6e8a893b41f98df18d9643c91713
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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