Trifluoroacetic acid → [4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanol

HRID 220561Notes

Reaction equation

HRID 220561 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:11]1([C:14]2[C:19]([C:20]3[CH:21]=[CH:22][C:23]([CH2:26][OH:27])=[CH:24][CH:25]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 685946841,1-Dimethylethyl 4-[3-[4-(hydroxymethyl)phenyl]-2-pyrazinyl]-1-piperazinecarboxylate

Product 1

HCID 68594908[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanolYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3′-(4-hydroxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (0.560 g, 1.51 mmol) in DCM (10 mL) and add trifluoroacetic acid (2 mL) and allow the mixture to stir at room temperature for six hr. Evaporate the solution then dilute with DCM and wash with saturated sodium bicarbonate. Dry the organics over sodium sulfate then filter and evaporate. Chromatograph the residue over silica gel (eluting with 8:92 methanol (with 2 M ammonia):DCM), to give [4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-methanol as a yellow solid (340 mg, 83%). MS (ES): m/z=271 [M+H]+.

Workup

  1. customEvaporate the solution
  2. additionthen dilute with DCM
  3. washwash with saturated sodium bicarbonate
  4. dry with materialDry the organics over sodium sulfate
  5. filtrationthen filter
  6. customevaporate

Sources & evidence

ORD record
ord-40e5109b63ef423b9db8aa9405e0c479
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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