Allyl bromide → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(allyl)-2-oxopyrrolidine

HRID 323496Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:8]1=[O:20].O1C[CH2:31][CH2:30][CH2:29]1.C([Li])(CC)C.C(Br)C=C>C(OCC)(=O)C.CCCCCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)([CH2:31][CH:30]=[CH2:29])[C:8]1=[O:20]

Participants

Conditions

Temperature: -78 °C

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine (0.93 g, 2.86 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of sec-butyl lithium (2.64 mL, 1.3 M in hexane, 3.43 mmol). After 30 minutes, add allyl bromide (0.42 g, 3.43 mmol). After the addition is complete, warm to ambient temperature. After 3 hours, add water and extract three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexane 1/4 to give the title compound.

Workup

additionAfter the addition
temperaturewarm to ambient temperature
waitAfter 3 hours
extractionextract three times with ethyl acetate
dry with materialDry the combined organic layers over Na2SO4
filtrationfilter
concentrationconcentrate in vacuo
customto obtain a residue

Sources & evidence

ORD record: ord-ce9e10d494574582a4e83754b4e9b5b1
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Reaction notes

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