Hydrochloric Acid → (rac)-Methyl 2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetate

HRID 714106Notes

Reaction equation

HRID 714106 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[CH2:17][CH2:16][CH:15]([O:18][CH2:19][C:20]([O:22][C:23](C)(C)C)=[O:21])[C:11]=3[CH:12]=[N:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.O1CCOCC1>CO>[F:27][C:2]([F:1])([F:28])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]3[CH2:17][CH2:16][CH:15]([O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:11]=3[CH:12]=[N:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 71811491(rac)-tert-Butyl 2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetate

Product 1

HCID 71811490(rac)-Methyl 2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetateYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled (0° C.) solution of (rac)-tert-butyl 2-(4-(4-(trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetate (example 97) (102 mg, 0.26 mmol) in MeOH (4 mL) was added 4M HCl in dioxane (0.26 mL, 1.04 mmol) and the reaction mixture was stirred at room temperature for 16 h. The solution was cooled (0° C.) again and treated with 4M HCl in dioxane (0.39 mL, 1.56 mmol). After 1 h at room temperature, the solution was evaporated to dryness. The residue was suspended in EtOAc, filtered and dried to give the title compound (46 mg, 51%, 80% purity with 20% of corresponding acid) as a grey solid. MS: 352.5 (M+H+).

Workup

  1. temperatureThe solution was cooled (0° C.) again
  2. waitAfter 1 h at room temperature
  3. customthe solution was evaporated to dryness
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-5b76814f44f34568b35f6fadf71f85c8
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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