Trifluoroacetic acid → HCID 59606052, compound

HRID 1945515Notes

Reaction equation

HRID 1945515 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[CH2:13]2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596058423-(4-Methyl-3-oxopiperazin-1-yl)azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59606052HCID 59606052, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-methyl-3-oxopiperazin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (211 mg, 0.78 mmol) and TFA (2 mL) in DCM (4 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-1-methylpiperazin-2-one as a white solid (125 mg, 95%). 1H NMR (CDCl3, 300 MHz): δ 3.63 (m, 4 H); 3.37-3.27 (m, 3 H); 3.03 (s, 2 H); 2.96 (s, 3 H); 2.58 (t, J=5.6 Hz, 2 H); 2.13-1.97 (m, 1 H).

Workup

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

Sources & evidence

ORD record
ord-e2f812e85db044f6ad7e2cd8baef1fcb
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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