Sodium periodate → 1-Tert-butyl 4-methyl 4-(2-oxopropyl)piperidine-1,4-dicarboxylate

HRID 1848436Notes

Reaction equation

HRID 1848436 reaction equation
[CH3:1][C:2](=C)[CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.I([O-])(=O)(=O)=[O:23].[Na+]>O1CCOCC1.O.ClCCl.[Os](=O)(=O)(=O)=O>[O:23]=[C:2]([CH3:1])[CH2:3][C:4]1([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 867094431-tert-Butyl 4-methyl 4-(2-methylallyl)piperidine-1,4-dicarboxylate

Product 1

HCID 867094441-Tert-butyl 4-methyl 4-(2-oxopropyl)piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 1-tert-butyl 4-methyl 4-(2-methylallyl)piperidine-1,4-dicarboxylate (2.2 g, 7.4 mmol) in dioxane/water (60 mL, 1/1) under nitrogen was added osmium tetroxide (0.038 g, 0.15 mmol) and sodium periodate (2.88 g, 13.5 mmol). The mixture was stirred at room temperature for 3 hours. The mixture was then diluted with dichloromethane (50 mL), and washed with 20% Na2S2O3 (20 mL). The organic layers were combined and washed with brine (20 mL), dried over anhydrous sodium sulfate, and filtered. The filtrates were concentrated and the residue was purified by column chromatography eluting with 0-60% ethyl acetate/hexane to afford 1-tert-butyl 4-methyl 4-(2-oxopropyl)piperidine-1,4-dicarboxylate. LC-MS (IE, m/z): 322.26 (M+23)+.

Workup

  1. washwashed with 20% Na2S2O3 (20 mL)
  2. washwashed with brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrates were concentrated
  6. customthe residue was purified by column chromatography
  7. washeluting with 0-60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-26c5fd124d5c4401aa671d22ac9ab6e6
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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