Hydroxyamine hydrochloride → 3-{5-Fluoro-3-[4-(1-hydroxyiminoethyl)phenylthio]phenyl}-3-methoxy-1-(prop-2-ynyl)pyrrolidine

HRID 37561Notes

Reaction equation

HRID 37561 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:12]=[C:13]([C:18]3([O:26][CH3:27])[CH2:22][CH2:21][N:20]([CH2:23][C:24]#[CH:25])[CH2:19]3)[CH:14]=[C:15]([F:17])[CH:16]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[NH2:29][OH:30]>>[F:17][C:15]1[CH:16]=[C:11]([S:10][C:7]2[CH:6]=[CH:5][C:4]([C:1](=[N:29][OH:30])[CH3:2])=[CH:9][CH:8]=2)[CH:12]=[C:13]([C:18]2([O:26][CH3:27])[CH2:22][CH2:21][N:20]([CH2:23][C:24]#[CH:25])[CH2:19]2)[CH:14]=1

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19935835HCID 19935835, compound

Product 1

HCID 867486993-{5-Fluoro-3-[4-(1-hydroxyiminoethyl)phenylthio]phenyl}-3-methoxy-1-(prop-2-ynyl)pyrrolidineYield 96%

Procedure

Using an analogous procedure to that described in Example 27, 3-[3-(4-acetylphenylthio)-5-fluorophenyl]-3-methoxy-1-(prop-2-ynyl)pyrrolidine was reacted with hydroxylamine hydrochloride to give 3-{5-fluoro-3-[4-(1-hydroxyiminoethyl)phenylthio]phenyl}-3-methoxy-1-(prop-2-ynyl)pyrrolidine in 96% yield, m.p. 97°-99° C. (recrystallised from a mixture of hexane and diethyl ether).

Sources & evidence

ORD record
ord-2ed9b5c7395145b9baf2b01cf8744a7c
Source dataset
uspto-grants-1995_05
Patent number
US05420298

Reaction notes

Loading…