ChemicalBook CAS DataBase List N-Boc-3-pyrrolidinone

N-Boc-3-pyrrolidinone synthesis

13synthesis methods

Product Name:N-Boc-3-pyrrolidinone
CAS Number:101385-93-7
Molecular formula:C9H15NO3
Molecular Weight:185.22

N-Boc-3-pyrrolidinone is used in a study of asymmetric hydrogen-transfer bioreduction of ketones with Leifsonia alcohol dehydrogenase. N-Boc-3-pyrrolidinone can be synthesized by starting with Dess-Martin periodinane, add it in dry CH2Cl2 and stirred at RT for 2 days, then add sodium thiosulphate solution and filter the two layers. The aqueous layer was extracted with CH2Cl2, then wash dry and concentrate the combined organic layers, and use 30% EtOAc to purify the N-Boc-3-pyrrolidinone.

109431-87-0 Synthesis

109431-87-0
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101385-93-7
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Yield:101385-93-7 77.3%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 0 - 20; for 0.2 h;Inert atmosphere;

Steps:

1 Synthesis of tert-butyl 3-oxopyrrolidine-l-carboxylate:
To a stirred solution of tert-butyl (R)-3-hydroxypyrrolidine-l-carboxylate (Intermediate 8-step 1, 4.5 g, 24.1 mmol) in DCM (60 ml) under N₂atmosphere, was added DMP (20.45 g, 48.12 mmol) at 0 °C. The reaction mixture was allowed to room temperature and stirred for about 2 hours. After completion of the reaction (monitored by TLC), the reaction mixture was quenched with 1 : 1 mixture of saturated NaHC0₃and saturated Na₂S₂0₃solution. The reaction mixture was extracted with DCM (2x100 ml). The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to give the residue. Purification by column chromatography with EtOAc and hexane (15:85) to afford the desired compound (3.44 g, yield: 77.3%) as an oil. 1H NMR (300 MHz, CDC1₃): δ 3.80-3.75 (m, 4H), 2.61-2.56 (m, 2H), 1.48 (s, 9H)

References:

HETERO RESEARCH FOUNDATION;BANDI, Parthasaradhi Reddy;KURA, Rathnakar Reddy;ADULLA, Panduranga Reddy;GAZULA LEVI, David Krupadanam;MUKKERA, Venkati;NEELA, Sudhakar;LANKA, Vl Subrahmanyam WO2017/17630, 2017, A1 Location in patent:Page/Page column 56

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