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

HRID 553479Notes

Reaction equation

HRID 553479 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][O:27][CH3:28])=[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>ClCCl>[CH3:28][O:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]2[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:15][CH:16]=[CH:17][N:18]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673673293'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl ester

Product 1

HCID 673675443'-(4-Methoxymethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinylYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3′-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (3.72 g, 9.70 mmol) in dichloromethane (25 mL). Add cold trifluoroacetic acid (30 mL, 44.2 g, 388 mmol, 40 eq.). Stir for 1 hr. Partition the crude reaction mixture between aq. 5N NaOH and dichloromethane. Separate the layers (pH aqueous layer=14). Extract the aqueous layer with dichloromethane (2×50 mL). Combine organic layers, dry over anhydrous Na2SO4, filter and concentrate to obtain the title preparation (2.76 g, 100% yield). LC MS (ES): m/z=285.0 [M+H].

Workup

  1. customPartition the crude
  2. customreaction mixture between aq. 5N NaOH and dichloromethane
  3. customSeparate the layers (pH aqueous layer=14)
  4. extractionExtract the aqueous layer with dichloromethane (2×50 mL)
  5. dry with materialCombine organic layers, dry over anhydrous Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto obtain the title
  9. custompreparation (2.76 g, 100% yield)

Sources & evidence

ORD record
ord-da032cba569d4f12b4208da11f4711fe
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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