Methyl (S) - 4 - Methylene - 1 - (benzyloxycarbonyl)pyrrolidine carboxylate synthesis
- Product Name:Methyl (S) - 4 - Methylene - 1 - (benzyloxycarbonyl)pyrrolidine carboxylate
- CAS Number:200184-60-7
- Molecular formula:C15H17NO4
- Molecular Weight:275.3
16217-15-5
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74-95-3
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200184-60-7
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$130.00/250MG
Yield:200184-60-7 81%
Reaction Conditions:
Stage #1: 1-benzyloxycarbonyl-4-oxo-L-proline methyl esterwith zinc;zirconocene dichloride in tetrahydrofuran at 20;Inert atmosphere;
Stage #2: 1,1-dibromomethane in tetrahydrofuran at 20 - 30;Inert atmosphere;
Steps:
9.2
Method V: Ketone (1.08 mmol), Zn (566 mg, 8.66 mmol), bis(cyclopentadienyl)zirconium dichloride (380 mg, 1.30 mmol), and THF (2 mL are combined and stirred at rt under nitrogen. Dibromomethane (0.17 mL, 2.44 mmol) is slowly added to the mixture. The internal temperature slowly increased to ca. 30° C. The reaction mixture is stirred for 3 h, and is quenched with water. The solution is extracted twice with ether. The organic layers are combined, dried over sodium sulfate, and concentrated under vacuum. The crude material is purified by column chromatography (SiO2, 30% ethyl acetate in hexanes).Step 2: (S)-1-Benzyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate is prepared from (S)-1-benzyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate following Method V (yield=81%). 1H NMR (300 MHz, CDCl3) δ 7.42-7.23 (m, 5H), 5.24-4.97 (m, 4H), 4.63-4.48 (m, 1H), 4.22-4.10 (m, 2H), 3.78-3.56 (m, 3H), 3.07-2.88 (m, 1H), 2.72-2.58 (m, 1H).
References:
US2010/22605,2010,A1 Location in patent:Page/Page column 35; 40-41
1779-49-3
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16217-15-5
84 suppliers
$87.00/250mg
200184-60-7
20 suppliers
$130.00/250MG
16217-15-5
84 suppliers
$87.00/250mg
200184-60-7
20 suppliers
$130.00/250MG
501-53-1
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84348-41-4
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200184-60-7
20 suppliers
$130.00/250MG
67-56-1
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501-53-1
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84348-38-9
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200184-60-7
20 suppliers
$130.00/250MG