Triacetoxyperiodinane → tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamate

HRID 1749516Notes

Reaction equation

HRID 1749516 reaction equation
[OH:1][CH:2]1[CH2:16][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:5]2)[CH2:16]1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 25324058tert-Butyl (6-hydroxyspiro[3.3]heptan-2-yl)carbamate

Product 1

HCID 39872257tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamateYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (6-hydroxyspiro[3.3]heptan-2-yl)carbamate (1.00 g, 4.40 mmol) in DCM (10 mL) was added Dess-Martin periodinane (2.80 g, 6.60 mmol) at ˜0° C. to 10° C. The resulting reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was treated with aqueous sodium bicarbonate and extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (22% ethyl acetate in petroleum ether) to afford the title compound (800 mg, 3.55 mmol, 80% yield) as a pale yellow solid. MS (ESI) m/z 226.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationConcentration under vacuum
  7. customgave the crude product, which
  8. customwas purified by silica gel column chromatography (22% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-aacccbede0bc4938b40f76b78f9a125c
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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