Propargyl bromide → HCID 19935825, compound

HRID 37556Notes

Reaction equation

[CH:1](N(C(C)C)CC)([CH3:3])[CH3:2].[C:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]2[CH:21]=[C:22]([C:26]3([O:31][CH3:32])[CH2:30][CH2:29][NH:28][CH2:27]3)[CH:23]=[CH:24][CH:25]=2)=[CH:15][CH:14]=1)(=[O:12])[CH3:11].C(Br)C#C>>[C:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19][C:20]2[CH:21]=[C:22]([C:26]3([O:31][CH3:32])[CH2:30][CH2:29][N:28]([CH2:3][C:1]#[CH:2])[CH2:27]3)[CH:23]=[CH:24][CH:25]=2)=[CH:17][CH:18]=1)(=[O:12])[CH3:11]

Participants

Reactant 3

HCID 7842Propargyl bromide

HCID 81531Diisopropylethylamine

HCID 199358543-[3-(4-Acetylphenylthio)phenyl]-3-methoxypyrrolidine

Product 1

HCID 19935825HCID 19935825, compoundYield 14%

Procedure

Using an analogous procedure to that described in Example 3 except that diisopropylethylamine was used in place of potassium carbonate, 3-[3-(4-acetylphenylthio)phenyl]-3-methoxypyrrolidine was reacted with 2-propynyl bromide to give 3-[3-(4-acetylphenylthio)phenyl]-3-methoxy-1-(prop-2-ynyl)pyrrolidine as a gum in 14% yield.

Sources & evidence

ORD record: ord-a72bfc29aa694c8c896f27081418a248
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420298

Reaction notes

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