Methanol → HCID 135848758, compound

HRID 346867Notes

Reaction equation

HRID 346867 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:41])=[C:18]([CH2:20][N:21]3[C:29]4[C:24](=[CH:25][C:26]([C:30]([OH:39])([C:35]([F:38])([F:37])[F:36])[C:31]([F:34])([F:33])[F:32])=[CH:27][CH:28]=4)[CH2:23][CH:22]3[CH3:40])[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CO>[Pd].O1CCCC1>[CH3:41][C:17]1[O:16][C:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[N:19][C:18]=1[CH2:20][N:21]1[C:29]2[C:24](=[CH:25][C:26]([C:30]([OH:39])([C:31]([F:34])([F:33])[F:32])[C:35]([F:36])([F:37])[F:38])=[CH:27][CH:28]=2)[CH2:23][CH:22]1[CH3:40]

Participants

5

Reactant 2

HCID 887MethanolHCID 11563244HCID 11563244, compound

Product 1

HCID 135848758HCID 135848758, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.2 g (2.1 mmol) of 2-{1-[2-(4-benzyloxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 79) in 15 ml of a 2:1-mixture of methanol and tetrahydrofuran was treated with 400 mg of Pd/C (10% Pd) and stirred vigorously under H2 at atmospheric pressure during 10 hrs. Filtration, evaporation of the solvent, and chromatography on silica gel with toluene/EtOAc (gradient from 9:1 to 1:1) gave 390 mg (39%) of 4-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-oxazol-2-yl}-phenol, light yellow foam, MS: 487 (MH+).

Workup

  1. filtrationFiltration, evaporation of the solvent, and chromatography on silica gel with toluene/EtOAc (gradient from 9:1 to 1:1)

Sources & evidence

ORD record
ord-74d890e7462c4f829b1c5795e79b9264
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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