Sodium Sulfite → Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate

HRID 1664791Notes

Reaction equation

HRID 1664791 reaction equation
[CH:1]1([C:4](=C)[CH2:5][CH:6]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:30].[Na+].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[CH:1]1([C:4](=[O:30])[CH2:5][CH:6]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 67440127Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate

Product 1

HCID 67439783Benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Osmium tetroxide (2.5 wt. % in t-BuOH; 17 uL, 0.001 mmol) was added to a solution of benzyl 4-[3-cyclopropyl-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate (173 mg, 0.45 mmol) in tetrahydrofuran (2 mL). Sodium periodate (290 mg, 1.35 mmol) in water (1.5 mL) was added to the reaction mixture. After 18 h, saturated aqueous sodium sulfite and saturated aqueous sodium bicarbonate were added and the mixture was extracted with ethyl acetate (4×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 388.1 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4×)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-745ec34c9e824b948431e9b6bd430826
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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