Hydrochloric Acid → HCID 69060100, compound

HRID 1435922Notes

Reaction equation

HRID 1435922 reaction equation
[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@:10](C(OCC)=O)([C:11](=[O:25])[NH:12][C:13]3[C:14]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:31]>O1CCOCC1>[ClH:31].[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:10]([C:11](=[O:25])[NH:12][C:13]3[C:14]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69059762HCID 69059762, compound

Product 1

HCID 69060100HCID 69060100, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (±)-cis-ethyl 2-benzyl-4-oxo-6-(trifluoromethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,4-c]quinoline-3a-carboxylate from Example 1, Part D (45 mg, 0.11 mmol) in 6 mL of 1,4-dioxane was added 4 mL of 3N HCl. The reaction was stirred at 90° C. for 18 h. The reaction was allowed to cool and was concentrated in vacuo. The residue was partitioned between ethyl acetate and sat'd aq NaHCO3. The organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was taken up in 3 mL of diethyl ether and then there was added HCl (0.10 mL of a 4N solution in 1,4-dioxane, 0.40 mmol). A solid settled out of solution. The solvents were decanted and the remaining solid was triturated twice with diethyl ether and dried in vacuo to afford 30 mg (73%) of the title compound of Example 2 as an off-white solid. LRMS (ESI): 347.26 (M+H)+.

Workup

  1. temperatureto cool
  2. concentrationwas concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. additionthere was added HCl (0.10 mL of a 4N solution in 1,4-dioxane, 0.40 mmol)
  8. customThe solvents were decanted
  9. customthe remaining solid was triturated twice with diethyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-5efd607c4f9249549a06eb04a1bf5f23
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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