Tetrahydrofuran → 1-(3,4,5-Trimethoxybenzyl)-3-(3-(t-butyldimethylsilyloxy)propyl)-2-oxopyrrolidine

HRID 323493

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([O:18][CH3:19])[C:15]=1[O:16][CH3:17])[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12].O1CCCC1.C([Li])(CC)C.[Si:30]([O:37][CH2:38][CH2:39][CH2:40]I)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([O:18][CH3:19])[C:15]=1[O:16][CH3:17])[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([CH2:40][CH2:39][CH2:38][O:37][Si:30]([C:33]([CH3:34])([CH3:36])[CH3:35])([CH3:31])[CH3:32])[C:8]1=[O:12]

Participants

Conditions

Temperature: -78 °C

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-2-oxopyrrolidine (0.84 g, 3.16 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of sec-butyl lithium (2.56 mL, 1.3 M in hexane, 3.33 mmol). After 30 minutes, add 3-(t-butyldimethylsilyloxy)propyl iodide (1.0 g, 3.33 mmol). After the addition is complete, warm to ambient temperature. After 2 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 to give the title compound.

Workup

additionAfter the addition
temperaturewarm to ambient temperature
waitAfter 2 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-cc292f7d6f9a45dc8e9ce1f2816341bd
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Linked notes

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