Sodium Hydroxide → 2-(7-(2,4-Bis(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid

HRID 2040536Notes

Reaction equation

HRID 2040536 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:4]=1[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[CH:16]([CH2:19][C:20]([O:22]CC)=[O:21])[CH2:17][CH2:18][C:10]=3[C:9]=2[CH:8]=1.[OH-].[Na+]>O1CCOCC1.O>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:28]=[C:27]([C:29]([F:31])([F:32])[F:30])[CH:26]=[CH:25][C:4]=1[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[CH:16]([CH2:19][C:20]([OH:22])=[O:21])[CH2:17][CH2:18][C:10]=3[C:9]=2[CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86653864Ethyl 2-(7-(2,4-Bis(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

Product 1

HCID 446240662-(7-(2,4-Bis(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic AcidYield 11.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-(7-(2,4-bis(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (0.191 g, 0.393 mmol) in dioxane (1.312 mL) and water (0.656 mL) was added NaOH (0.826 mL, 0.826 mmol). The mixture was heated under reflux for 2 h, cooled to room temperature and diluted with water. After washing with DCM, the aqueous layer was acidified with 1 M HCl and extracted with EtOAc (thrice). The combined extracts were washed with brine, dried over MgSO4 and concentrated to give the title compound as a magenta solid (19.9 mg). LCMS m/z=458.1 [M+H]+, 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03-2.13 (m, 1H), 2.35 (dd, J=15.98, 9.03 Hz, 1H), 2.58-2.78 (m, 4H), 3.41-3.52 (m, 1H), 5.31 (s, 2H), 6.72 (dd, J=8.78, 2.46 Hz, 1H), 6.92 (d, J=2.40 Hz, 1H), 7.23 (d, J=8.72 Hz, 1H), 7.99-8.19 (m, 3H), 10.52 (s, 1H), 12.19 (s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. washAfter washing with DCM
  4. extractionextracted with EtOAc (thrice)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-73ceb468a3724d46ad4351625b5b604c
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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