Dimethyl Sulfoxide → 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester

HRID 1617336Notes

Reaction equation

HRID 1617336 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.CS(C)=O.C(N(CC)CC)C>C(Cl)Cl>[O:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 3-hydroxyazetidine-1-carboxylate (10.0 g, 57.7 mmol), dimethyl sulfoxide (24.0 mL, 338 mmol), triethylamine (40 mL, 300 mmol) and methylene chloride (2.0 mL) was added sulfur trioxide-pyridine complex (40 g, 200 mmol) portionwise at 0° C. The mixture was stirred for 3 hours, quenched with brine, and extracted with methylene chloride. The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column (0-6% ethyl acetate (EtOAc) in hexanes) to give tert-butyl 3-oxoazetidine-1-carboxylate (5.1 g, 52% yield).

Workup

  1. additionwas added sulfur trioxide-pyridine complex (40 g, 200 mmol) portionwise at 0° C
  2. customquenched with brine
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column (0-6% ethyl acetate (EtOAc) in hexanes)

Sources & evidence

ORD record
ord-df2f64daedb84c0eb1d9092e70bf10f6
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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