Trifluoroacetic acid → 4-(Azetidin-3-yl)thiomorpholine 1,1-dioxide

HRID 1945502Notes

Reaction equation

HRID 1945502 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596054113-(1,1-Dioxo-1-thiomorpholine-4-YL)azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 597519614-(Azetidin-3-yl)thiomorpholine 1,1-dioxideYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(1,1-dioxo-1-thiomorpholin-4-yl)-azetidine-1-carboxylic acid tert-butyl ester (3.35 g, 11.5 mmol) and TFA (15 mL) in DCM (30 mL) was stirred at room temperature for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording 4-Azetidin-3-yl-thiomorpholine 1,1-dioxide as a white solid (2.0 g, 91%). 1H NMR (CDCl3, 300 MHz): δ 3.64-3.53 (m, 4 H); 3.49-3.39 (m, 1 H); 3.08 (m, 4 H); 2.86-2.79 (m, 4 H); 1.83 (s, 1 H).

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-cc066ef626884b3b82b98dfa4150ce15
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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