Divinyl sulfone → 3-(1,1-Dioxo-1-thiomorpholine-4-YL)azetidine-1-carboxylic acid tert-butyl ester

HRID 1945501Notes

Reaction equation

HRID 1945501 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH2:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:13]([S:15]([CH:18]=[CH2:19])(=[O:17])=[O:16])=[CH2:14]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:12]2[CH2:19][CH2:18][S:15](=[O:17])(=[O:16])[CH2:13][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6496Divinyl sulfoneHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Product 1

HCID 596054113-(1,1-Dioxo-1-thiomorpholine-4-YL)azetidine-1-carboxylic acid tert-butyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a refluxing solution of 3-aminoazetidine-1-carboxylic acid tert-butyl ester (10.0 g, 58.1 mmol) in EtOH (50 mL) was added drop wise a solution of divinyl sulfone (5.9 mL, 6.86 g, 58.1 mmol) in EtOH (50 mL). The resulting mixture was stirred at reflux for 15.5 h, cooled to room temperature and concentrated in vacuo. The resulting beige solid was triturated with Et2O, affording the title compound as a white solid (10.8 g, 64%). 1H NMR (CDCl3, 300 MHz): δ 3.97 (dd, J=8.8, 7.1 Hz, 2 H); 3.76 (dd, J=8.8, 7.1 Hz, 2 H); 3.36-3.26 (m, 1 H); 3.13-3.05 (m, 4 H); 2.90-2.83 (m, 4 H); 1.44 (s, 9 H).

Workup

  1. temperatureat reflux for 15.5 h
  2. concentrationconcentrated in vacuo
  3. customThe resulting beige solid was triturated with Et2O

Sources & evidence

ORD record
ord-d51f104a9a4c4585946976e5a571a499
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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