Triacetoxyperiodinane → tert-butyl 2-oxo-7-azaspiro[4.5]decane-7-carboxylate

HRID 1478002Notes

Reaction equation

HRID 1478002 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][C:4]2([CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:6][CH2:5][C:4]2([CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118173835HCID 118173835, compound

Product 1

HCID 118173849tert-butyl 2-oxo-7-azaspiro[4.5]decane-7-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-hydroxy-7-azaspiro[4.5]decane-7-carboxylate (252 mg, 1.0 mmol) in DCM (5 mL) was added Dess-Martin periodinane (0.84 g, 1.99 mmol). The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the title compound as yellow oil (197 mg, 79%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5)

Sources & evidence

ORD record
ord-fb8eae203431443e8718c5672c0bbb74
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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