Hydrochloric Acid → 2-Methyl-6,7-bis(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]

HRID 1405366Notes

Reaction equation

HRID 1405366 reaction equation
[CH3:1][N:2]1[C:18]2([CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)[C:6]2=[CH:7][C:8]([C:14]([F:17])([F:16])[F:15])=[C:9]([C:10]([F:13])([F:12])[F:11])[N:5]2[CH2:4][CH2:3]1.Cl>C(Cl)Cl>[CH3:1][N:2]1[C:18]2([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:6]2=[CH:7][C:8]([C:14]([F:15])([F:16])[F:17])=[C:9]([C:10]([F:12])([F:11])[F:13])[N:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86668522Tert-butyl 2-methyl-6,7-bis(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 866685232-Methyl-6,7-bis(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4'-piperidine]Yield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-methyl-6,7-bis(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (from step 1) was taken up in CH2Cl2 (2 mL) and HCl (1.7 mL of 4 M, 6.8 mmol) was added. The mixture was allowed to stir for 30 min before it was concentrated under reduced pressure. The residue was taken up in ethyl acetate and was washed with sat. aq. NaHCO3, then brine. The organic layer was dried over sodium sulfate, filtered and concentrated to give 2-methyl-6,7-bis(trifluoromethyl)spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine] (22 mg, 2% over 2 steps). ESI-MS m/z calc. 341.1, found 342.3 (M+1)+; Retention time: 1.29 minutes.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. washwas washed with sat. aq. NaHCO3
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d4e71b4771dd402d8749bac0aa421aa2
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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