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Hydrochloric Acid → (rac)-2-(4-(4-(Trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetic acid hydrochloride

HRID 714107
Notes
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Reaction equation

HRID 714107 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(C)(C)C)=[O:21])[C:11]=3[CH:12]=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[ClH:29].O1CCOCC1>C(Cl)Cl>[ClH:29].[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]([OH:22])=[O:21])[C:11]=3[CH:12]=[N:13][CH:14]=2)=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 89846289(rac)-2-(4-(4-(Trifluoromethyl)phenyl)-6,7-dihydro-5H-cyclopenta[c]pyridin-7-yloxy)acetic acid hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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) (235 mg, 0.597 mmol) in CH2Cl2 (2 mL) was added 4M HCl in dioxane (1.49 mL, 5.97 mmol) and the reaction mixture was stirred at room temperature for 16 h. The mixture was evaporated to dryness to give the title compound (221 mg, 99%) as a grey solid. MS: 338.5 (M+H+).

Workup

  1. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-4572692cf41c443a9b94326ca38bf257
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187429B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes