Triacetoxyperiodinane → HCID 131734834, compound

HRID 1778561Notes

Reaction equation

HRID 1778561 reaction equation
[OH:1][CH:2]1[CH2:7][CH:6]2[N:8]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH:3]1[CH2:4][C@H:5]2[C:19]([O:21][CH2:22][CH3:23])=[O:20].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH:6]2[N:8]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH:3]1[CH2:4][C@H:5]2[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131734832HCID 131734832, compound

Product 1

HCID 131734834HCID 131734834, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of O7-benzyl O5-ethyl (5R)-2-hydroxy-7-azabicyclo[2.2.1]heptane-5,7-dicarboxylate (0.37 g, 1.1 mmol), Dess-martin reagent (1.38 g, 3.3 mmol) in DCM (50 mL) was stirred for 12 hours. After removal of solvent, the residue was purified by silica gel chromatography to give O7-benzyl O5-ethyl (5R)-2-oxo-7-azabicyclo[2.2.1]heptane-5,7-dicarboxylate 151e. Yield: 90%. MS: calc'd (MH +) 304, measured (MH +) 304.

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d91d6000c8bf4eefa7475c94e79a73f2
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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