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

HRID 2274071Notes

Reaction equation

HRID 2274071 reaction equation
[CH:1]1([CH2:7][C:8]2[CH:33]=[CH:32][C:11]([CH2:12][O:13][C:14]3[CH:22]=[CH:21][C:20]4[NH:19][C:18]5[CH:23]([CH2:26][C:27]([O:29]CC)=[O:28])[CH2:24][CH2:25][C:17]=5[C:16]=4[CH:15]=3)=[CH:10][C:9]=2[C:34]([F:37])([F:36])[F:35])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>O1CCOCC1>[CH:1]1([CH2:7][C:8]2[CH:33]=[CH:32][C:11]([CH2:12][O:13][C:14]3[CH:22]=[CH:21][C:20]4[NH:19][C:18]5[CH:23]([CH2:26][C:27]([OH:29])=[O:28])[CH2:24][CH2:25][C:17]=5[C:16]=4[CH:15]=3)=[CH:10][C:9]=2[C:34]([F:37])([F:35])[F:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67211498Ethyl 2-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

Product 1

HCID 446242702-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic AcidYield 51.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ethyl 2-(7-(4-(cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (40 mg, 0.078 mmol) in dioxane was added 1 M LiOH aqueous solution (0.39 mL, 0.39 mmol). The reaction mixture was stirred at room temperature for 5 h. The solvent was partly removed, then diluted with water, acidified with HCl solution. The pinkish solid was collect and dried to give the title compound (19.5 mg). LCMS m/z=486.3 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 0.96-1.06 (m, 2H), 1.14-1.22 (m, 3H), 1.55-1.70 (m, 6H), 2.05-2.10 (m, 1H), 2.40 (dd, J=16.0 and 9.0 Hz, 1H), 2.62-2.75 (m, 6H), 3.42-3.50 (m, 1H), 5.12 (s, 2H), 6.72 (dd, J=8.7 and 2.4 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 7.21 (d, J=8.8 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.66 (d, J=7.8 Hz, 1H), 7.75 (s, 1H), 10.48 (s, 1H), 12.20 (br, 1H).

Workup

  1. customThe solvent was partly removed
  2. additiondiluted with water
  3. customThe pinkish solid was collect
  4. customdried

Sources & evidence

ORD record
ord-2001c85e32664ff9a38aac9115acbe1f
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

Loading…