Water → 2-(3,3-Dimethylbutyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 1963265Notes

Reaction equation

HRID 1963265 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][CH:5]1[CH2:10][CH:9]([CH2:11][OH:12])[CH2:8][CH2:7][N:6]1[C:13]([O:15][CH3:16])=[O:14].[Na].[OH2:20]>C(Cl)(Cl)(Cl)Cl.C(#N)C.C(Cl)Cl.[Ru](Cl)(Cl)Cl>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([OH:20])=[O:12])[CH2:8][CH2:7][N:6]1[C:13]([O:15][CH3:16])=[O:14]

Participants

8

Reactant 3

HCID 962Water2×HCID 5360545SodiumHCID 66735064Methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 667317342-(3,3-Dimethylbutyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acidYield 94%

Reagents, catalysts & solvents 4

HCID 61850Ruthenium trichlorideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylate (2.44 g, 9.49 mmol) was dissolved in CCl4 (20 mL) and acetonitrile (20 mL). Sodium periodiate (6.09 g, 28.5 mmol) was added followed by water (30 mL) and ruthenium (III) chloride (43 mg, 0.21 mmol). The resulting suspension was stirred at room temperature for 3 h 50 min. The reaction mixture was diluted with DCM (100 mL) and water (100 mL). The aqueous layer was extracted with DCM (×3) and the combined organic phase passed through a phase separator and evaporated to yield crude 2-(3,3-dimethylbutyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (2.42 g, 94%) as a black solid. MS m/z 272 (M+H)+

Workup

  1. extractionThe aqueous layer was extracted with DCM (×3)
  2. customevaporated

Sources & evidence

ORD record
ord-2d90ddcdd9c449bc9e819e93ec0b9120
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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