(S)-1-benzyl 2-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate synthesis
- Product Name:(S)-1-benzyl 2-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate
- CAS Number:147489-27-8
- Molecular formula:C17H21NO5
- Molecular Weight:319.35
115-11-7
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Yield:147489-27-8 100%
Reaction Conditions:
with sulfuric acid in dichloromethane; for 12 h;Cooling with ice;
Steps:
General method for tert-butyl protection
General procedure: 3 or 9 was dissolved in dichloromethane (1.2 L), and cooled to 0 °C in an ice bath. To this stirred solution, concentrated H2SO4 (9 mL, 162mmol) was added dropwise, after which 2-methylprop-1-ene was bubbled into the solution (~50% increase in total reaction volume), and reacted overnight (12h). After completion of the reaction (monitored by TLC), saturated NaHCO3 (300 mL) was added to neutralize the sulfuric acid (final pH ~8). The mixture was concentrated in vacuo, and the emulsion extracted with EtOAc (3 x 500 mL). The organic layer was washed with brine (3 x 200 mL), dried with Na2SO4, and concentrated in vacuo to yield a light-yellow, viscous oil. Yield was quantitative, and product was utilized in the next step without purification.
References:
Cheong, Jae Eun;Pfeiffer, Conrad T.;Northrup, Justin D.;Parker, Matthew F.L.;Schafmeister, Christian E. [Tetrahedron Letters,2016,vol. 57,# 44,p. 4882 - 4884] Location in patent:supporting information
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