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
24424-99-5
362706-25-0
Step 5: Synthesis of tert-butyl 5-methyl-(pyrrolidin-3-one)-1-carboxylate 1-Benzyl-5-methylpyrrolidin-3-one (2 g, 10.57 mmol) and di-tert-butyl dicarbonate (Boc2O, 2.77 g, 12.98 mmol) were dissolved in ethanol (EtOH, 20 mL) and palladium/carbon (Pd/C, 0.3 g) was added as a catalyst. The reaction mixture was stirred overnight under hydrogen (H2, 40 psi) atmosphere. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by column chromatography (eluent ratio petroleum ether/ethyl acetate = 9:1) to afford tert-butyl 5-methyl-(pyrrolidin-3-one)-1-carboxylate (1.4 g, 66.5% yield) as a colorless oil. Product characterization data: 1H NMR (400 MHz, CDCl3) δ ppm 7.33-7.23 (m, 5H), 4.18-4.15 (d, J=13.2 Hz, 1H), 3.29-3.14 (m, 1H), 2.99-2.93 (m, 1H), 2.65-2.60 (m, 1H), 2.51-2.45 (m , 1H), 2.16-2.08 (m, 1H), 1.34-1.32 (m, 3H); no ionization signal was detected by ES-LCMS.
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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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