Trifluoroacetic acid → hexahydro-2H-pyrazino[1,2-a]pyrazin-1(6H)-one

HRID 2074866Notes

Reaction equation

HRID 2074866 reaction equation
CC(OC([NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH:12]1[C:24]([O:26]CC)=O)=O)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:24]1(=[O:26])[NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH:12]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 592158481-(1,1-Dimethylethyl) 3-ethyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,3-piperazinedicarboxylate

Product 1

HCID 45122044hexahydro-2H-pyrazino[1,2-a]pyrazin-1(6H)-oneYield 38.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1,1-dimethylethyl) 3-ethyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1,3-piperazinedicarboxylate (D77, 2.492 g, 6.21 mmol) in dichloromethane (30 mL) kept at 0° C. was added TFA (10 mL) dropwise. The solution was kept at 0° C. for 2 h, and then at room temperature for 6 h. The deprotected product was isolated by SCX and the resulting solution was evaporated at 50° C. to induce cyclization. The target product was purified by reverse phase chromatography (Oasis HLB 6 g×4 columns, eluted with water), obtaining 372 mg of the title compound.

Workup

  1. customkept at 0° C.
  2. waitat room temperature for 6 h
  3. customThe deprotected product was isolated by SCX
  4. customthe resulting solution was evaporated at 50° C.
  5. customThe target product was purified by reverse phase chromatography (Oasis HLB 6 g×4 columns, eluted with water)

Sources & evidence

ORD record
ord-e6c4c14b430b47b4ab2b1fb17e6dcf55
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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