HCID 11613417, compound → HCID 21082191, compound

HRID 346868Notes

Reaction equation

HRID 346868 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[O:11][C:12]([CH3:36])=[C:13]([CH2:15][N:16]3[C:24]4[C:19](=[CH:20][C:21]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:22][CH:23]=4)[CH2:18][CH:17]3[CH3:35])[N:14]=2)[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:32][C:30]([F:31])([F:33])[C:25]([C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:16]([CH2:15][C:13]1[N:14]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=3)[O:11][C:12]=1[CH3:36])[CH:17]([CH3:35])[CH2:18]2)([OH:34])[C:26]([F:29])([F:28])[F:27]

Participants

4

Reactant 2

HCID 11613417HCID 11613417, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21082191HCID 21082191, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.25 g (2.37 mmol) of 3-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-oxazol-2-yl}-benzoic acid methyl ester (example 90) in 15 ml of THF was treated at 0° C. with 180 mg (4.73 mmol) of lithium aluminium hydride and allowed to reach RT within 3 hrs. Distribution of the crude between a saturated aqueous solution of NH4Cl and EtOAc, drying of the combined organic phases over Na2SO4 and evaporation of the solvent gave 1.1 g (93%) of 1,1,1,3,3,3-hexafluoro-2-{1-[2-(3-hydroxymethyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-2-methyl-2,3-dihydro-1H-indol-5-yl}-propan-2-ol, off-white foam, MS: 499 (M−H)−.

Workup

  1. dry with materialDistribution of the crude between a saturated aqueous solution of NH4Cl and EtOAc, drying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-0ffe58f12a6d42bca085a287f25450fe
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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