Triethylamine → 3-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

HRID 322070Notes

Reaction equation

CCN([CH2:6][CH3:7])CC.[C:8](Cl)(=[O:13])[C:9](C)(C)[CH3:10].[O:15]1[CH2:19][CH2:18][NH:17][C:16]1=[O:20].[Li]CCCC.[Li].[C:27]([O:30][CH2:31][CH3:32])(=[O:29])[CH3:28]>C1COCC1>[CH3:28][C:27]1([CH2:6][CH2:7][CH2:10][CH2:9][C:8]([N:17]2[CH2:18][CH2:19][O:15][C:16]2=[O:20])=[O:13])[O:29][CH2:32][CH2:31][O:30]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 2-2 (16.0 g, 85.5 mmol), NEt3 (13.1 ml, 94.1 mmol) and THF (400 mL) at −78° C. was added pivaloyl chloride (11.6 ml, 94.1 mmol). The mixture was warmed to 0° C. for 1.0 h and then recooled to −78° C. To a stirred solution of 2-oxazolidinone (9.3 g, 106.9 mmol) and THF (200 ml) at −78° C. was added nBuLi (43.0 ml, 106.9 mmol, 2.5M in hexanes) dropwise over 10 minutes. After 20 minutes, the lithium reagent was transferred to the mixed anhydride via cannula. After 10 minutes, the reaction was warmed to 0° C. for 1.0 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes) to give 2-3 as a colorless foam.

Workup

customrecooled to −78° C
waitAfter 10 minutes
temperaturethe reaction was warmed to 0° C. for 1.0 h
washwashed with sat. NaHCO3, brine
dry with materialdried over MgSO4
customremoval of the solvent
customthe residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-ba4689a5c6be4bc5ad66c4444783f98b
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211191B1

Reaction notes

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