Hydroxyamine hydrochloride → 3-{2-[4-(1-Hydroxyiminoethyl)phenylthio]thien-5-yl}-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine

HRID 37559Notes

Reaction equation

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

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 199358063-[2-(4-Acetylphenylthio)thien-5-yl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine

Product 1

HCID 867486973-{2-[4-(1-Hydroxyiminoethyl)phenylthio]thien-5-yl}-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidineYield 63%

Procedure

Using an analogous procedure to that described in Example 27, 3-[2-(4-acetylphenylthio)thien-5-yl]-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine was reacted with hydroxylamine hydrochloride to give 3-{2-[4-(1-hydroxyiminoethyl)phenylthio]thien-5-yl}-3-methoxy-1-(2,2,2-trifluoroethyl)pyrrolidine as a gum in 63% yield.

Sources & evidence

ORD record: ord-a465c113fb3143f7b0110f62b2c0a2d9
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420298

Reaction notes

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