Water → HCID 21082202, compound

HRID 1724049Notes

Reaction equation

HRID 1724049 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:36])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:20][CH:21]=4)[C:16]([CH:33]=[O:34])=[C:15]3[CH3:35])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:36])=[C:11]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][C:19]([C:23]([OH:32])([C:28]([F:29])([F:30])[F:31])[C:24]([F:25])([F:26])[F:27])=[CH:20][CH:21]=4)[C:16]([CH2:33][OH:34])=[C:15]3[CH3:35])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 21082195HCID 21082195, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21082202HCID 21082202, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 50 mg of 1-[2-(3-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-3-carbaldehyde in 1 mL of THF was treated at 0° C. with 5 mg (0.14 mmol) of LiAlH4 and allowed to reach RT within 1 h. Ice cubes were added and the mixture distributed between Et2O and H2O. Drying of the combined organic phases over Na2SO4 and evaporation of the solvent yielded 36 mg of 2-{1-[2-(3-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-3-hydroxymethyl-2-methyl-1H-indol-5-yl}-1,1,1,3,3,3-hexafluoro-propan-2-ol, off white solid, 533 (MH+).

Workup

  1. additionIce cubes were added
  2. dry with materialDrying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-65a73360106842de95734c23d12c361d
Source dataset
uspto-grants-2009_02
Patent number
US07485652B2

Reaction notes

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