(R)-TERT-BUTYL 2-(CYANOMETHYL)PYRROLIDINE-1-CARBOXYLATE synthesis
- Product Name:(R)-TERT-BUTYL 2-(CYANOMETHYL)PYRROLIDINE-1-CARBOXYLATE
- CAS Number:201039-13-6
- Molecular formula:C11H18N2O2
- Molecular Weight:210.27
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Yield: 84%
Reaction Conditions:
in dimethyl sulfoxide at 90; for 7 h;
Steps:
1.3
(R)-2-Cyanomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester: A solution of (R)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (11.50 g, 32.39 mmol) and sodium cyanide (4.76 g, 97.18 mmol) in dimethylsulfoxide (115 mL) was stirred at about 90° C. for about 7 hours. Following standard extractive workup with ethyl acetate, the crude residue was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to yield the title product as an oil (5.70 g, 84%). [α]D20 +87.2° (c 0.9, chloroform); 1H NMR (400 MHz, DMSO-d6) δ 1.41 (s, 9H), 1.70-1.84 (m, 2H), 1.86-2.00 (m, 1H), 2.03-2.14 (m, 1H), 2.71-2.90 (m, 2H), 3.20-3.32 (m, 2H), 3.85-3.95 (m, 1H); IR (film) υ 2975, 2885, 2248, 1693, 1462, 1397, 1254 cm-1; MS 211 (M+1).
References:
AUSPEX PHARMACEUTICALS, INC. US2009/203763, 2009, A1 Location in patent:Page/Page column 33
![tert-butyl (2R)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate](/CAS/20200331/GIF/132482-10-1.gif)
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201039-13-6
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