ChemicalBook CAS DataBase List (R)-(+)-1-Boc-3-aminopyrrolidine

(R)-(+)-1-Boc-3-aminopyrrolidine synthesis

6synthesis methods

Product Name:(R)-(+)-1-Boc-3-aminopyrrolidine
CAS Number:147081-49-0
Molecular formula:C9H18N2O2
Molecular Weight:186.25

143700-04-3

147081-49-0

A mixture of tert-butyl (R)-3-azido pyrrolidine-1-carboxylate (250 mg, 1.18 mmol) and Pd/C (50 mg, 10% w/w) in methanol (10 mL) was reacted with stirring at room temperature for 12 h under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford tert-butyl (R)-3-aminopyrrolidine-1-carboxylate as a colorless liquid (210 mg, 96% yield). The product was characterized by 1H NMR (600 MHz, CDCl3): δ 3.33-3.49 (m, 3H), 3.27-3.32 (m, 1H), 2.95-3.03 (m, 1H), 1.98-2.08 (m, 1H), 1.63-1.70 (m, 1H), 1.41 (s, 9H). Mass spectrometry (MS-ESI) analysis showed: m/z 131.20 [M-55]+.

143700-04-3
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147081-49-0
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Yield:147081-49-0 96%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 20; for 12 h;

Steps:

72.1
A mixture of (R) -tert-butyl 3-azidopyrrolidine-1-carboxylate (250 mg, 1.18 mmol) and Pd/C (10, 50 mg) in methanol (10 mL) was stirred at rt under H₂ at atmospheric pressure for 12 h and filtered. The filtrate was concentrated to give (R) -tert-butyl 3-aminopyrrolidine-1-carboxylate as colorless liquid (210 mg, 96) .¹H NMR (600 MHz, CDCl₃) : δ ppm 3.39-3.49 (m, 3H) , 3.27-3.32 (m, 1H) , 2.95-3.03 (m, 1H) , 1.98-2.08 (m, 1H) , 1.63-1.70 (m, 1H) , 1.41 (s, 9H) and MS-ESI: m/z 131.20 [M-55] ⁺.

References:

SUNSHINE LAKE PHARMA CO., LTD.;ZHANG, Yingjun;LIU, Bing;YU, Tianzhu;ZHANG, Xiangyu;ZHANG, Shiguo;ZHANG, Jiancun;CHENG, Changchung WO2016/34134, 2016, A1 Location in patent:Paragraph 00508

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132945-75-6 Synthesis