Trifluoroacetic acid → HCID 59606190, compound

HRID 1922694Notes

Reaction equation

HRID 1922694 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[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[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596061821-Azetidinecarboxylic acid, 3-(2-oxo-1-pyrrolidinyl)-, 1,1-dimethylethyl ester

Product 1

HCID 59606190HCID 59606190, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(2-oxopyrrolidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (320 mg, 1.33 mmol) and TFA (1.5 mL) in DCM (3 mL) was stirred at room temperature for 4 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH/DCM and eluted with 2M NH3/MeOH affording 1-Azetidin-3-ylpyrrolidin-2-one as a white solid (174 mg, 93%). 1H NMR (CDCl3, 300 MHz): γ 5.05 (m, 1H), 3.85-3.76 (m, 4H), 3.61 (m, 2H), 2.41 (m, 2H) and 2.07 (m, 2H)

Workup

  1. washwashed with MeOH/DCM
  2. washeluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-64b1584c3ce64ad5a53f79f3f815949b
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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