Methylparaben → 3-Phenoxy-4,5-dihydroisoxazole

HRID 1746137Notes

Reaction equation

HRID 1746137 reaction equation
Br[C:2]1[CH2:6][CH2:5][O:4][N:3]=1.COC(=O)[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>>[O:16]([C:2]1[CH2:6][CH2:5][O:4][N:3]=1)[C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 7456MethylparabenHCID 219834983-Bromo-4,5-dihydroisoxazole

Product 1

HCID 149604673-Phenoxy-4,5-dihydroisoxazole

Procedure

3-phenoxy-4,5-dihydroisoxazole I-177a and I-177b were prepared in 2 steps from racemic compound I-14. Bromo-4,5-dihydroisoxazole I-14 was reacted with 4-hydroxybenzoic acid methyl ester using Method 5 followed by hydroysis using the analogous conditions as in Example 94. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=368.0 m/z. Activity: B

Workup

  1. customThese compounds can be separated

Sources & evidence

ORD record
ord-002998902f4d4a03bf906a7adaa4428d
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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