Hydrochloric Acid → trans-2-[6-(Trifluoromethyl)pyridin-3-yl]cyclopropanecarboxylic acid

HRID 572019Notes

Reaction equation

HRID 572019 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[N:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2[C:12]([O:14]C)=[O:13])=[CH:5][CH:4]=1.Cl>C1COCC1.O>[F:16][C:2]([F:1])([F:17])[C:3]1[N:8]=[CH:7][C:6]([C@@H:9]2[CH2:11][C@H:10]2[C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66691074trans-Methyl 2-[6-(trifluoromethyl)pyridin-3-yl]cyclopropanecarboxylate

Product 1

HCID 66689840trans-2-[6-(Trifluoromethyl)pyridin-3-yl]cyclopropanecarboxylic acidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 26B (22 mg, 0.09 mmol) in THF (1 mL) at ambient temperature was added LiOH monohydrate (11 mg, 0.26 mmol) as a slurry in H2O (0.500 mL). The reaction was left to stir for 14 h, acidified to pH 4 via 1N HCl(aq), and then extracted with EtOAc (3×10 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated under reduced pressure to give 16 mg 26C (79% yield). m/z (ES+) M+1=232.0; HPLC tR=1.86 min. 1H NMR (500 MHz, MeOH-d4) δ 8.56 (d, J=2.1 Hz, 1H), 7.78-7.65 (m, 2H), 2.62-2.47 (m, 1H), 1.97 (ddd, J=9.0, 4.7, 4.6 Hz, 1H), 1.63 (ddd, J=9.4, 5.0, 4.8 Hz, 1H), 1.49-1.39 (m, 1H).

Workup

  1. waitThe reaction was left
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30fcb4da5bee4a69a9dd917fd85361be
Source dataset
uspto-grants-2015_05
Patent number
US09029381B2

Reaction notes

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