Propargyl bromide → 3-Methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]-1-(prop-2-ynyl)pyrrolidine

HRID 37548Notes

Reaction equation

HRID 37548 reaction equation
[CH3:1][O:2][C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:26](Br)[C:27]#[CH:28]>>[CH3:1][O:2][C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH:9]=2)[CH2:7][CH2:6][N:5]([CH2:28][C:27]#[CH:26])[CH2:4]1

Participants

3

Reactant 2

HCID 7842Propargyl bromideHCID 19935823HCID 19935823, compound

Product 1

HCID 199358073-Methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]-1-(prop-2-ynyl)pyrrolidineYield 11%

Procedure

Using an analogous procedure to that described in Example 3, 3-methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]pyrrolidine was reacted with prop-2-ynyl bromide to give 3-methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]-1-(prop-2-ynyl)pyrrolidine, m.p. 63°-65° C., in 11% yield.

Sources & evidence

ORD record
ord-e6c7b8400c1d40b6b84a845acffe390b
Source dataset
uspto-grants-1995_05
Patent number
US05420298

Reaction notes

Loading…