ChemicalBook CAS DataBase List 1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 2-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (2R)-

1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 2-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (2R)- synthesis

6synthesis methods

Product Name:1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 2-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (2R)-
CAS Number:870097-43-1
Molecular formula:C17H21NO5
Molecular Weight:319.35

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1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 2-(1,1-dimethylethyl) 1-(phenylmethyl) ester, (2R)-

870097-43-1
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Yield:870097-43-1 100%

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

98946-18-0 Synthesis