tert-Butanol → HCID 15411266, compound

HRID 1862476Notes

Reaction equation

HRID 1862476 reaction equation
[Na].C(O)(C)(C)C.C(OCC)(=O)C.[C:13]([O:17][C:18]([N:20]1[CH:24]2[CH2:25][CH2:26][CH:21]1[C:22](S(C1C=CC(C)=CC=1)(=O)=O)=[CH:23]2)=[O:19])([CH3:16])([CH3:15])[CH3:14]>[Hg].C(O)(C)(C)C.C(OCC)(=O)C>[C:13]([O:17][C:18]([N:20]1[CH:24]2[CH2:25][CH2:26][CH:21]1[CH:22]=[CH:23]2)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 5360545SodiumHCID 14936170HCID 14936170, compound

Product 1

HCID 15411266HCID 15411266, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 18619786HCID 18619786, compoundSolvent

Procedure

A 2.5% Na amalgam was prepared by adding sodium (15.1 g, 657 mmol) slices to mercury (56 mL, 3.77 mol). This amalgam was added in portions to a vigorously stirring solution of NaH2PO4 (24.4 g, 203 mmol) and Na2HPO4 (28.9 g, 203 mmol) in a 1:1 tert-butanol:ethyl acetate mixture (100 mL). A solution of 7-tert-Butoxycarbonyl-2-p-tolylsulfonyl-7-azabicyclo[2.2.1]-hepta-2-ene (14.22 g, 40.7 mmol) in a 1:1 tert-butanol-ethyl acetate mixture (200 mL) was added to the stirring mixture at 0° C. After stirring for 24 h the mixture was decanted into a separatory funnel and extracted with ethyl acetate. The remaining mercury was washed thoroughly with ethyl acetate. The combined organic layers were dried with sodium sulfate, concentrated, then purified by flash chromatography with 4:1 hexane:ethyl acetate to provide 7-tert-Butoxycarbonyl-7-azabicyclo[2.2.1]hept-2-ene (3-56 g, 45% based on recovered starting material) as a colorless oil.

Workup

  1. customwas decanted into a separatory funnel
  2. extractionextracted with ethyl acetate
  3. washThe remaining mercury was washed thoroughly with ethyl acetate
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatography with 4:1 hexane

Sources & evidence

ORD record
ord-43c8a5be8f7640aeb6d8a1ed13bf568c
Source dataset
uspto-grants-2003_03
Patent number
US06538010B1

Reaction notes

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