Pyridine → N-(t-butyldimethylsilyl)-3-azido-4-(2-oxoethyl)azetidin-2-one

HRID 1154914Notes

Reaction equation

HRID 1154914 reaction equation
N1C=CC=CC=1.[Si:7]([N:14]1[CH:17]([CH2:18][CH2:19][OH:20])[CH:16]([N:21]=[N+:22]=[N-:23])[C:15]1=[O:24])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[Si:7]([N:14]1[CH:17]([CH2:18][CH:19]=[O:20])[CH:16]([N:21]=[N+:22]=[N-:23])[C:15]1=[O:24])([C:10]([CH3:12])([CH3:13])[CH3:11])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 1049PyridineHCID 20563655N-(t-butyldimethylsilyl)-3-azido-4-(2-hydroxyethyl)-azetidin-2-one

Product 1

HCID 20563653N-(t-butyldimethylsilyl)-3-azido-4-(2-oxoethyl)azetidin-2-one

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Chromium trioxide (0.06 mol) is added to a solution of pyridine (0.12 mol) in methylene chloride (150 ml) and the mixture is stirred at room temperature for 15 min. A solution of N-(t-butyldimethylsilyl)-3-azido-4-(2-hydroxyethyl)-azetidin-2-one (0.01 mol) in methylene chloride (10 ml) is then added all at once. After stirring at room temperature for 5 min, the mixture is decanted and the dark, gummy residue is washed with more methylene chloride. The combined methylene chloride supernatant is concentrated under vacuum to a residue which is taken up in ether and filtered through celite. The filtrate is washed with 5% hydrochloric acid, 5% sodium bicarbonate solution, and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to yield N-(t-butyldimethylsilyl)-3-azido-4-(2-oxoethyl)azetidin-2-one.

Workup

  1. stirringAfter stirring at room temperature for 5 min
  2. customthe mixture is decanted
  3. washthe dark, gummy residue is washed with more methylene chloride
  4. concentrationThe combined methylene chloride supernatant is concentrated under vacuum to a residue which
  5. filtrationfiltered through celite
  6. washThe filtrate is washed with 5% hydrochloric acid, 5% sodium bicarbonate solution, and brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-eeff3208236047618ed2cc451d04a4a7
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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