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

HRID 706975Notes

Reaction equation

HRID 706975 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 265C (8.0 g) in dichloromethane (200 mL) was added Dess-Martin Periodinane (11.2 g). The mixture was stirred overnight. The mixture was diluted with ethyl acetate (400 mL) and washed with 2N aqueous NaOH, water, and brine. After drying over Na2SO4 and filtration, concentration of the solvent gave the crude product which was used directly in the next reaction without further purification.

Workup

  1. washwashed with 2N aqueous NaOH, water, and brine
  2. dry with materialAfter drying over Na2SO4 and filtration, concentration of the solvent

Sources & evidence

ORD record
ord-59326fe062da47d98e35682368f451f6
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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