Dichloromethane → [4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanol dihydrochloride
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:36]>>[ClH:36].[ClH:36].[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]1Participants
Procedure
Dissolve 3′-(4-hydroxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (2.76 g, 7.45 mmol) in DCM (25 mL) and add trifluoroacetic acid (5 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), then dissolve the solid in methanol and add ammonium chloride then sonicate the mixture for 10 min. Evaporate the solution to give [4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-methanol dihydrochloride as a white solid (1.303 g, 65%). MS (ES): m/z=271 [M+H]+.
Workup
- customEvaporate the solution
- additionthen dilute with DCM
- washwash with saturated sodium bicarbonate
- dry with materialDry the organics over sodium sulfate
- filtrationthen filter
- customevaporate
- dissolutionChromatograph the residue over silica gel (eluting with 8:92 methanol (with 2 M ammonia):DCM), then dissolve the solid in methanol
- additionadd ammonium chloride
- customthen sonicate the mixture for 10 min
- customEvaporate the solution
Sources & evidence
- ORD record
- ord-4bb3cdcb86504f3cb354cd2f4cd87ebb
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202873B2
Reaction notes
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