Benzyl Alcohol → 2-Benzyloxy-1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]ethanol

HRID 1528959Notes

Reaction equation

HRID 1528959 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]2[CH2:16][O:15]2)=[CH:4][CH:3]=1.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCO>[CH2:17]([O:24][CH2:16][CH:14]([C:9]1[C:10]([CH3:13])=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[OH:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 866524045-(4-Bromo-phenyl)-3-methyl-4-oxiranyl-isoxazole

Product 1

HCID 665773582-Benzyloxy-1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared according to the procedure described in Example 34, Step 4, using 5-(4-Bromo-phenyl)-3-methyl-4-oxiranyl-isoxazole and benzyl alcohol. After the reaction the material was submitted to chiral preparatory HPLC (Chiralcel AS Column, 2% EtOH in hexanes, 65 minute run). The first enantiomer off of the column is Enantiomer A.

Workup

  1. customPrepared
  2. customAfter the reaction the material

Sources & evidence

ORD record
ord-4760dea1205c44d38cef6031c1289b92
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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