Trifluoroacetic acid → HCID 11637045, compound

HRID 1435930Notes

Reaction equation

HRID 1435930 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[NH:11][CH2:10][C@@H:9]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C@@H:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[NH:11][CH2:10][C@@H:9]3[CH2:13][NH:14][CH2:15][C@@H:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131727756HCID 131727756, compound

Product 1

HCID 11637045HCID 11637045, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-cis tert-butyl 6-methoxy-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate (25 mg, 0.082 mmol) in 4 mL methylene chloride was added 1 mL trifluoroacetic acid. The reaction was allowed to stir at ambient temperature for 2 h and then was concentrated in vacuo to afford a TFA salt. This material was free-based by partitioning between methylene chloride and aq. ammonium hydroxide. The organics were washed with brine, dried (Na2SO4) and concentrated to afford 10 mg (60%) of the title compound of Example 10. 1H NMR (CDCl3): δ 6.76-6.62 (m, 3H), 4.42 (broad s, 1H), 3.85 (s, 3H), 3.50-3.23 (overlapping m, 5H), 2.98-2.80 (m, 2H), 2.65-2.57 (m, 1H). LRMS (ESI): 205.3 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-b97f0f6393434913b1dc75cfa200cbee
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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