Triacetoxyperiodinane → tert-Butyl 4-[4-(methoxycarbonyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]piperidine-1-carboxylate

HRID 1867602Notes

Reaction equation

HRID 1867602 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([NH:36][C:37]([NH:39][C@H:40]([C:43]([O:45][CH3:46])=[O:44])[CH2:41]O)=[O:38])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[CH3:46][O:45][C:43]([C:40]1[NH:39][C:37](=[O:38])[N:36]([CH:33]2[CH2:32][CH2:31][N:30]([C:28]([O:27][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:29])[CH2:35][CH2:34]2)[CH:41]=1)=[O:44]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68566174Methyl N-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)serinate

Product 1

HCID 68564149tert-Butyl 4-[4-(methoxycarbonyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1.77 g, 4.16 mmol) was added to a solution of methyl N-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)serinate (1.15 g, 3.33 mmol) in dichloromethane (30 mL) at 0° C. and then warmed to ambient temperature. 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, and concentrated. Purification by silica gel chromatography (100% dichloromethane→12% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound.

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→12% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-828b2c2be8174508a67433fa4246a31e
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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