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

HRID 1725644Notes

Reaction equation

HRID 1725644 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+]>C1COCC1.O.[O-]S([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 THF (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 Na2SO3 and NaHCO3 and extracted with ethyl acetate (4×). The combined organic washes were dried over sodium sulfate, filtered and evaporated. The crude product was purified by silica gel chromatography, eluting with a gradient of 50 to 100% EtOAc:hexanes to give the title compound (2.39 g). MS: m/z=348.1 (M+1).

Workup

  1. extractionextracted with ethyl acetate (4×)
  2. dry with materialThe combined organic washes were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of 50 to 100% EtOAc

Sources & evidence

ORD record
ord-1ffed2019c9f4afeba41589828126113
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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