Triacetoxyperiodinane → Benzyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1848931Notes

Reaction equation

HRID 1848931 reaction equation
[OH:1][CH:2]1[CH2:22][CH2:21][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(OCC)(=O)C>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67126666HCID 67126666, compound

Product 1

HCID 59803011Benzyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 391C (23.66 g) in dichloromethane (350 mL) was added Dess-Martin Periodinane (33.1 g). The mixture was stirred overnight. The mixture was diluted with ethyl acetate (600 mL) and washed with 2N aqueous NaOH, water, and brine. After drying over Na2SO4, the mixture was filtered and concentrated to provide the title compound.

Workup

  1. washwashed with 2N aqueous NaOH, water, and brine
  2. dry with materialAfter drying over Na2SO4
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3a2afa4e14e34e0697ebb0f5109e8379
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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