Water → HCID 11548102, compound

HRID 346860Notes

Reaction equation

HRID 346860 reaction equation
C[O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[N:7][C:6]=1[CH2:17][N:18]1[C:26]2[C:21](=[CH:22][C:23]([C:27]([OH:36])([C:32]([F:35])([F:34])[F:33])[C:28]([F:31])([F:30])[F:29])=[CH:24][CH:25]=2)[CH:20]=[C:19]1[CH3:37])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.O>C1COCC1>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[O:9][C:5]([CH2:3][OH:2])=[C:6]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([OH:36])([C:32]([F:34])([F:35])[F:33])[C:28]([F:30])([F:29])[F:31])=[CH:24][CH:25]=3)[CH:20]=[C:19]2[CH3:37])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 86601374HCID 86601374, compound

Product 1

HCID 11548102HCID 11548102, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., a solution of 10 mg (0.018 mmol) of 2-(2-chloro-phenyl)-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-indol-1-ylmethyl]-oxazole-5-carboxylic acid methyl ester (example 130) in 0.3 mL of THF was treated with 1 mg (0.026 mmol) of LiAlH4 and stirred at RT for 6 hrs. Ice was added and the mixture distributed between Et2O and water. Drying of the combined organic phases and evaporation yielded 9 mg (95%) of 2-{1-[2-(2-chloro-phenyl)-5-hydroxymethyl-oxazol-4-ylmethyl]-2-methyl-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol, off-white solid, MS:518 (MH+), 1 Cl.

Workup

  1. additionIce was added
  2. customDrying of the combined organic phases and evaporation

Sources & evidence

ORD record
ord-c68b1dbf0149416c8576a189aa0b21ea
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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