1-BOC-5-Methyl-3-pyrrolidinone synthesis
- Product Name:1-BOC-5-Methyl-3-pyrrolidinone
- CAS Number:362706-25-0
- Molecular formula:C10H17NO3
- Molecular Weight:199.25
23770-07-2
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Yield: 66.5%
Reaction Conditions:
with hydrogen;palladium on carbon in ethanol under 2068.65 Torr;
Steps:
I.7.5
Step 5: terf-butyl 5-methyl-(pyrrolidin-3-one)-1-carboxylateA solution of 1-benzyl-5-methylpyrrolidin-3-one (2 g, 10.57 mmol), BoC2O (2.77 g, 12.98 mmol) and Pd/C (0.3 g) in EtOH (20 mL) was stirred under H2 (40 psi) overnight. After TLC showed the reaction was complete, the reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (9:1 PE/EA) to give terf-butyl 5-methyl-(pyrrolidin-3-one)-1-carboxylate (1.4 g, 66.5%) as colorless oil (1.4 g, 66.5%): 1H NMR (400 MHz, CDCI3) δ ppm 7.33-7.23 (m, 5H), 4.18-4.15 (d, J = 13.2 Hz, 1 H), 3.29-3.14 (m, 1 H), 2.99-2.93 (m, 1 H), 2.65-2.60 (m, 1 H), 2.51-2.45 (m, 1 H), 2.16-2.08 (m, 1 H), 1.34-1.32 (m, 3H); ES-LCMS does not ionize.
References:
GLAXOSMITHKLINE LLC;CHRISTENSEN, Siegfried, Benjamin, IV;QIN, Donghui;CHEN, Shenglin;HUANG, Xing;LI, Di;LI, Fei;LI, Lei;LIN, Xiaojuan;LU, Shi;LU, Zhen;LV, Maoyun;WANG, Chuanning;WU, Chengde;XIAO, Mei;YU, Haiyu;ZHANG, Weina;ZHANG, Zhiliu WO2010/141539, 2010, A1 Location in patent:Page/Page column 24-25
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