Water → 3-Tetrahydropyranyloxyethyl-3-(3,4-dichlorophenyl)pyrrolidine

HRID 975080Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:14][CH2:13][NH:12][C:11]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:14][CH2:13][NH:12][CH2:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

The 3-(2-tetrahydropyranyloxyethyl)-3-(3,4-dichlorophenyl)-2-pyrrolidinone (3.9 grams prepared as described supra) is dissolved in 50 ml of tetrahydrofuran and the solution is added to a suspension of 0.9 grams of lithium aluminum hydride in 5 ml of tetrahydrofuran heated to 60° C. The reaction mixture is then heated for one hour at 60° C. and then cooled. To the resulting mixture 1 ml of water, 1 ml of 4N sodium hydroxide, and 3 ml of water are added sequentially. The insoluble portion is removed by filtration and the filtrate is concentrated in vacuo. The residue is taken up in diethyl ether, dried over magnesium sulfate, and concentrated under vacuum to give the desired intermediate.

Workup

temperatureThe reaction mixture is then heated for one hour at 60° C.
temperaturecooled
customThe insoluble portion is removed by filtration
concentrationthe filtrate is concentrated in vacuo
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-4a32565795134832a6cfda64f0cdca81
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05607947

Reaction notes

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