N-Iodosuccinimide → HCID 118037682, compound

HRID 2272491Notes

Reaction equation

HRID 2272491 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[C:19](=[O:36])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25][CH2:24]2)[C:19](=[O:36])[C:18]=1[I:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 118038096HCID 118038096, compound

Product 1

HCID 118037682HCID 118037682, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Iodosuccinimide (2.85 g) was added at room temperature to an acetic acid (57.6 mL) solution of tert-butyl 4-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylate (4.43 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was rendered basic by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate twice. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (4.83 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe obtained organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-68d242f09fce49669cec3deb1174ae5d
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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