Triacetoxyperiodinane → tert-Butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1,4-dioxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1501821Notes

Reaction equation

HRID 1501821 reaction equation
[OH:1][CH:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:5](=[O:19])[N:4]([C:20]2[CH2:21][O:22][C:23](=[O:26])[C:24]=2[CH3:25])[CH2:3]1.C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[CH3:25][C:24]1[C:23](=[O:26])[O:22][CH2:21][C:20]=1[N:4]1[CH2:3][C:2](=[O:1])[C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[C:5]1=[O:19]

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86709492tert-Butyl 4-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 86709494tert-Butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1,4-dioxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Procedure

To tert-butyl 4-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (see example I-37A and I-37B, Step C, racemate prior to chiral HPLC separation)(200 mg, 0.546 mmol) in DCM (2.8 mL) was added sodium bicarbonate (68.8 mg, 0.819 mmol) and Dess-Martin periodinane (347 mg, 0.819 mmol). The reaction mixture was vigorously stirred for 1.5 h, then quenched with 10% Na2S2O3 and NaHCO3 aqueous solutions, and stirred for 20 min. The aqueous layer was extracted with DCM, and the organic layers were washed with brine, dried, and concentrated to give tert-butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1,4-dioxo-2,8-diazaspiro[4.5]decane-8-carboxylate. LCMS: [(M+1)]+=365

Workup

  1. customand I-37B, Step C, racemate prior to chiral HPLC separation)(200 mg, 0.546 mmol) in DCM (2.8 mL)
  2. customquenched with 10% Na2S2O3 and NaHCO3 aqueous solutions
  3. stirringstirred for 20 min
  4. extractionThe aqueous layer was extracted with DCM
  5. washthe organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e0fd3cd11f5b42cfaf5f4340f5326655
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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