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

HRID 1501755Notes

Reaction equation

HRID 1501755 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 acetatehexane 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 acetatehexane

Sources & evidence

ORD record
ord-be3f3bc26003456e96ec4c9f653fb4ab
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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