Triacetoxyperiodinane → tert-Butyl 4-[4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]piperidine-1-carboxylate

HRID 1867599Notes

Reaction equation

HRID 1867599 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)=O.[Si:23]([O:40][CH2:41][CH:42]([NH:45][C:46]([NH:48][CH:49]1[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]1)=[O:47])[CH2:43]O)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)C1C=CC=CC=1>ClCCl>[Si:23]([O:40][CH2:41][C:42]1[NH:45][C:46](=[O:47])[N:48]([CH:49]2[CH2:50][CH2:51][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:53][CH2:54]2)[CH:43]=1)([C:36]([CH3:39])([CH3:37])[CH3:38])([C:11]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68568228tert-Butyl 4-[({[2-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)ethyl]amino}carbonyl)amino]piperidine-1-carboxylate

Product 1

HCID 68567938tert-Butyl 4-[4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]piperidine-1-carboxylateYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (53 mg, 0.126 mmol) was added to a solution of tert-butyl 4-[({[2-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)ethyl]amino}carbonyl)amino]piperidine-1-carboxylate (50 mg, 0.090 mmol) in dichloromethane (20 mL) at 0° C. After 4 h, the reaction was quenched with a 1:1 mixture of saturated sodium thiosulfate and sodium bicarbonate solution. The mixture was extracted with dichloromethane (2×) and the combined organic extracts were dried over sodium sulfate, filtered, concentrated. Purification by silica gel chromatography (100% dichloromethane→9% methanol {1% ammonium hydroxide)/dichloromethane} gave the title compound (25 mg). MS 536.3 (M+1)

Workup

  1. customthe reaction was quenched with a 1:1 mixture of saturated sodium thiosulfate and sodium bicarbonate solution
  2. extractionThe mixture was extracted with dichloromethane (2×)
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→9% methanol {1% ammonium hydroxide)/dichloromethane}

Sources & evidence

ORD record
ord-22ac656291e2477aa0e718cb19651602
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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