Lithium Hydroxide → 3-[2-Methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-benzoic acid

HRID 1724034Notes

Reaction equation

HRID 1724034 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:17][CH:18]=3)[CH2:13][CH:12]2[CH3:30])[CH:5]=1.[Li+].[OH-]>C1COCC1>[CH3:30][CH:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[C:16]([C:20]([OH:29])([C:21]([F:24])([F:23])[F:22])[C:25]([F:27])([F:28])[F:26])[CH:15]=2)[N:11]1[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:31])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 116837873-[2-Methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-benzoic acid methyl ester

Product 1

HCID 116044473-[2-Methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-benzoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 66 mg (0.118 mmol) of 3-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-benzoic acid methyl ester (example 61) in 0.5 mL of THF was treated with 0.2 mL of a 1M aqueous LiOH solution and stirred for 10 hrs at RT. The solvents were evaporated and the residue distributed between EtOAc and a aqueous solution of NH4Cl. Drying of the combined organic phases over Na2SO4 and evaporation of the solvent yielded 51 mg (99%) of 3-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-benzoic acid, light yellow gum, MS: 432 (M−H)−.

Workup

  1. customThe solvents were evaporated
  2. dry with materialDrying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-247b8a0d7e104a628b1708b3a07ec14e
Source dataset
uspto-grants-2009_02
Patent number
US07485652B2

Reaction notes

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