Triethylamine → 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester

HRID 1926656Notes

Reaction equation

HRID 1926656 reaction equation
[C:1]([N:8]1[CH2:11][C:10]([OH:12])=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.S(=O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O>[O:12]=[C:10]1[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 68668960HCID 68668960, compound

Product 1

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-boc-3-(hydroxyl)azetine (1.0 g, 5.8 mmol) and triethylamine (1.6 mL, 12 mmol) in CH2Cl2 (10 mL) and DMSO (4 mL) at 0° C. was added pyridine sulfur trioxide (1.8 g, 12 mmol). The reaction was allowed to warm to room temperature. After 18 h, the reaction mixture was partitioned between CH2Cl2 (100 mL) and 1M aqueous citric acid solution (100 mL). The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to afford tert-butyl 3-oxoazetidine-1-carboxylate as a crude oil. 1H NMR (600 MHz, DMSO-D6) 4.67 (s, 4H); 1.47 (s, 9H).

Workup

  1. customthe reaction mixture was partitioned between CH2Cl2 (100 mL) and 1M aqueous citric acid solution (100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3fa602d81d6240318aca7e0631d0e31d
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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