Sodium periodate → Benzyl 4-[1-(ethoxycarbonyl)-3-oxobutyl]piperidine-1-carboxylate

HRID 1664779Notes

Reaction equation

HRID 1664779 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1)[CH2:7][C:8](C)=[CH2:9])=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:28].[Na+]>O1CCCC1.O.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Os](=O)(=O)(=O)=O>[CH2:1]([O:3][C:4]([CH:6]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:13][CH2:12]1)[CH2:7][C:8](=[O:28])[CH3:9])=[O:5])[CH3:2]

Participants

8

Reactant 2

HCID 23667635Sodium periodateHCID 67440198HCID 67440198, compound

Product 1

HCID 67438602Benzyl 4-[1-(ethoxycarbonyl)-3-oxobutyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 24437Sodium SulfiteSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Osmium tetroxide (2.5 wt. % in t-BuOH; 0.3 mL, 0.001 mmol) was added to a solution of benzyl 4-[1-(ethoxycarbonyl)-3-methylbut-3-en-1-yl]piperidine-1-carboxylate (2.88 g, 8.01 mmol) in tetrahydrofuran (30 mL). Sodium periodate (5.14 g, 24.0 mmol) in water (26 mL) was added to the reaction mixture. After 5 days, the reaction was diluted with saturated aqueous sodium sulfite and saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic washes were dried over sodium sulfate, filtered and concentrated to give the title compound. MS 362.2 (M+1).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. dry with materialThe combined organic washes were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c123988e375f4549b825bfee6118452f
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

Loading…