(2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester synthesis
- Product Name:(2S-trans)-4-Azido-1,2-pyrrolidinedicarboxylic Acid 1-(1,1-DiMethylethyl) 2-Methyl Ester
- CAS Number:121147-97-5
- Molecular formula:C11H18N4O4
- Molecular Weight:270.285
![1,2-Pyrrolidinedicarboxylic acid, 4-[(Methylsulfonyl)oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S,4S)-](/CAS/20150408/GIF/121147-93-1.gif)
121147-93-1
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Yield:121147-97-5 95%
Reaction Conditions:
with sodium azide in N,N-dimethyl-formamide at 0 - 80; for 4 h;
Steps:
ii 1-(tert-Butyl) 2-methyl (2S,4R)-4-azidopyrrolidine-1,2-dicarboxylate
To a stirred solution of 1-(tert-butyl) 2-methyl (2S,4S)-4-((methylsulfonyl)oxy)pyrrolidine-1,2- dicarboxylate (500 g, 1548.0 mmol, 1.0 eq) in DMF (5000 mL) was added NaN3 (139.3 g, 2322.0 mmol, 1.5 eq) portionwise at 0 °C. The reaction mixture was gradually heated to 80 °C for 4 h. The resulting reaction mixture was cooled to rt and poured into ice cold water (3500 mL) and extracted with EtOAc (3 x 3000 mL). The organic phases were combined and washed with ice cold water (4 x 1000 mL) and brine (2 x 1000 mL), dried over Na2SO4 and concentrated under reduced pressure to afford 1-(tert-butyl) 2-methyl (2S,4R)-4-azidopyrrolidine-1,2-dicarboxylate as a brown semi-solid (400 g, 1481.5 mmol, 95% yield). (0220) LCMS: Method C, 1.65 min, MS: ES+ 271.2; 1H NMR (400 MHz, DMSO-d6) d ppm: 4.36 - 4.39 (m, 1H), 4.20 - 4.27 (m, 1H), 3.65 - 3.68 (m, 3H), 3.51 - 3.58 (m, 1H), 3.38 - 3.41 (d, 1H), 2.29 - 2.38 (m, 1H), 2.10 - 2.19 (m, 1H), 1.40 (s, 4.5H, Boc rotamer 1), 1.34 (s, 4.5H, Boc rotamer 2). Further sub- title compound (400 g, 1470 mmol, 95% yield) was prepared by an identical method on a 252 g scale in duplicate.
References:
WO2020/212350,2020,A1 Location in patent:Page/Page column 28-29
74844-91-0
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![1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)-](/CAS/20210305/GIF/146060-25-5.gif)
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88043-21-4
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