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

HRID 246779Notes

Reaction equation

HRID 246779 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1.S(=O)(=O)=O.N1C=CC=CC=1>CS(C)=O>[O:8]=[C:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterYield 100.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Triethylamine (2.47 mL) was added to a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (0.5 g, 2.9 mmol) in DMSO (5 mL). To this mixture, a solution of pyridine sulphur trioxide (1.8 g, 11.3 mmol) in DMSO (6.5 mL) was added drop-wise and the mixture was stirred at room temperature for 1.5 hrs. The mixture was poured onto ice-water and extracted with ethyl acetate (3×50 mL), organics combined dried with sodium sulfate, filtered and concentrated to afford tert-butyl 3-oxoazetidine-1-carboxylate as white solid (500 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 4.68 (s, 4H), 1.48 (s, 9H).

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialorganics combined dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ece05f837024a7e95067a9c4510f1df
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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