dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate synthesis
- Product Name:dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate
- CAS Number:607362-87-8
- Molecular formula:C15H19NO4
- Molecular Weight:277.32
93102-05-7
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607362-87-8
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Yield:607362-87-8 86.02%
Reaction Conditions:
with trifluoroacetic acid in dichloromethane at 0 - 20; for 6 h;Inert atmosphere;
Steps:
22.1 dimethyl l-benzylpyrrolidine-3,4-dicarboxylate
To a solution of dimethyl maleate (4.00 g) in CH2C12 ( 100 mL) was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine ( 1.2 eq) followed by a solution of TFA in CH2C12 (0.1 eq, 1 M) dropwise at 0 °C under N2,. The reation mixture was heated to room temperature and stirred for 6 h, washed with water followed by brine. The mixture was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 3: 1 (v/v) PE/EA) to yield the title compound (6.62 g, 86.02 %). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 278(?+1);? NM (400 MHz, CDC13) ?: 2.70-2.75 (m, 2H), 3.12-3.17 (m, 1 H), 3.30-3.33 (m, 2H), 3.66 (s, 6H), 7.24-7.31 (m, 5H).
References:
WO2013/71697,2013,A1 Location in patent:Paragraph 00290
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607362-87-8
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