Hydroxyamine hydrochloride → 3-{3-[4-(1-Hydroxyiminoethyl)phenylthio]phenyl}-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine

HRID 37560Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:12]=[C:13]([C:17]3([O:27][CH3:28])[CH2:21][CH2:20][N:19]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[NH2:30][OH:31]>>[OH:31][N:30]=[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:12]=[C:13]([C:17]3([O:27][CH3:28])[CH2:21][CH2:20][N:19]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:18]3)[CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 199358023-[3-(4-Acetylphenylthio)phenyl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine

Product 1

HCID 867486983-{3-[4-(1-Hydroxyiminoethyl)phenylthio]phenyl}-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidineYield 63%

Procedure

Using an analogous procedure to that described in Example 27, 3-[3-(4-acetylphenylthio)phenyl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine was reacted with hydroxylamine hydrochloride to give 3-{3-[4-(1-hydroxyiminoethyl)phenylthio]phenyl}-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine in 63% yield, m.p. 86°-88° C.

Sources & evidence

ORD record: ord-a774af4983804e779369059ae14a670d
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420298

Reaction notes

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