Dichloromethane → Trans-2-(3,4-dihydroxybenzyl)-5-[2-(4-hydroxyphenyl)ethyl]pyrrolidine hydrobromide

HRID 1249514Notes

Reaction equation

Cl.C[O:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[O:26]C)[CH2:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[NH:9]1.C(Cl)Cl.B(Br)(Br)[Br:32]>CO>[BrH:32].[OH:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[OH:26])[CH2:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[NH:9]1

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of 1 g. (0.003 mole) of trans-2-(3,4-dimethoxybenzyl)-5-[2-(4-methoxyphenyl)ethyl]pyrrolidine hydrochloride in 35 ml. of methylene chloride was cooled to -65° C. and treated with 2.68 g. (0.012 mole) of boron tribromide dropwise. The reaction mixture was then stirred under N2 and slowly warmed from -65° to room temperature over the course of one hour and 25 minutes. The solution was then cooled again to -60° C. and 25 ml. of methanol was cautiously added. Solvent was removed in vacuo, more methanol was added and some insoluble material was filtered off. After removal of methanol in vacuo, the residue was treated with ethyl acetate. Upon standing at room temperature, 0.8 g. of product was obtained as an off-white solid, m.p. 202°-203° C.

Workup

additiontreated with 2.68 g
temperatureslowly warmed from -65° to room temperature over the course of one hour and 25 minutes
customSolvent was removed in vacuo, more methanol
additionwas added
filtrationsome insoluble material was filtered off
customAfter removal of methanol in vacuo
additionthe residue was treated with ethyl acetate
customUpon standing at room temperature
customof product was obtained as an off-white solid, m.p. 202°-203° C.

Sources & evidence

ORD record: ord-ff1d1fd1d6b041a98244d1f39f15a108
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04632929

Reaction notes

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