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

HRID 1664775Notes

Reaction equation

HRID 1664775 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12][CH2:11]1)[CH2:7][CH:8]=C)=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:27].[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:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:12][CH2:11]1)[CH2:7][CH:8]=[O:27])=[O:5])[CH3:2]

Participants

8

Reactant 2

HCID 23667635Sodium periodateHCID 67441606Ethyl 1-[(phenylmethoxy)carbonyl]-α-2-propen-1-yl-4-piperidineacetate

Product 1

HCID 86616780Benzyl 4-[1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylateYield 58.3%

Reagents, catalysts & solvents 5

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

Procedure

Benzyl 4-[1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate (4.08 g, 11.8 mmol) was dissolved in tetrahydrofuran (45 mL), and osmium tetroxide (0.45 mL, 2.5% solution in t-butanol) was added followed by a solution of sodium periodate (7.57 g, 35.4 mmol) in water (37 mL). After 24 h, the reaction was diluted with saturated aqueous sodium sulfite and saturated aqueous sodium bicarbonate and extracted with ethyl acetate (4×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (50% hexanes/ethyl acetate→100% ethyl acetate) to give the title compound (2.39 g). MS 348.1 (M+1).

Workup

  1. extractionextracted with ethyl acetate (4×)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (50% hexanes/ethyl acetate→100% ethyl acetate)

Sources & evidence

ORD record
ord-4eb0e6e3db2e4afa87e8b6978aa79058
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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