N-Boc-3-pyrrolidinone

Bezeichnung:N-Boc-3-pyrrolidinone

CAS-Nr101385-93-7

Englisch Name:N-Boc-3-pyrrolidinone

CBNumberCB2740029

SummenformelC9H15NO3

Molgewicht185.22

MOL-Datei101385-93-7.mol

N-Boc-3-pyrrolidinone physikalisch-chemischer Eigenschaften

Schmelzpunkt	34-38 °C (lit.)
Siedepunkt	270.9±33.0 °C(Predicted)
Dichte	1.133±0.06 g/cm3(Predicted)
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	Dichloromethane, Ethyl Acetate, Methanol
pka	-1.79±0.20(Predicted)
Aggregatzustand	Low Melting Solid
Farbe	White to yellow to orange
Wasserlöslichkeit	Insoluble in water.
InChI	InChI=1S/C9H15NO3/c1-9(2,3)13-8(12)10-5-4-7(11)6-10/h4-6H2,1-3H3
InChIKey	JSOMVCDXPUXKIC-UHFFFAOYSA-N
SMILES	N1(C(OC(C)(C)C)=O)CCC(=O)C1
CAS Datenbank	101385-93-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-37/38-41-36/37/38-20/21/22
S-Sätze:	26-36/37/39-36
WGK Germany	3
Hazard Note	Irritant
HS Code	29339900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

N-Boc-3-pyrrolidinone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
N-Boc-3-pyrrolidinone is an organic compound insoluble in water. It is a starting material for the synthesis of spirocyclic tetrahydrofuran and is also used in studies related to the preparation of 5-membered heterocyclic secondary alcohols with carrot as a biocatalyst^[1].
Chemische Eigenschaften
Brown Oil
Verwenden
Used in a study of asymmetric hydrogen-transfer bioreduction of ketones with Leifsonia alcohol dehydrogenase.
Verwenden
In the Synthesis and antibacterial evaluation of a novel series of rifabutin-like spirorifamycins 1-Boc-3-pyrrolidinone is used.
Synthese

83220-73-9

101385-93-7

General procedure for the synthesis of 1-tert-butoxycarbonyl-3-hydroxy-pyrrolidine from 1-tert-butoxycarbonyl-3-pyrrolidinone: To a dichloromethane (20 mL) solution of oxalyl chloride (2.8 mL, 32.4 mmol) a dichloromethane (40 mL) solution of dimethylsulfoxide (DMSO, 4.6 mL, 64.8 mmol) was slowly added at -78 °C, and subsequently the reaction mixture was stirred at -15 °C for 5 min. Next, a dichloromethane (60 mL) solution of N-Boc-3-pyrrolidinol (4.04 g, 21.6 mmol) was added at -78°C and stirring was continued for 2 hours at this temperature. Subsequently, triethylamine (15 mL, 108 mmol) was added to the reaction mixture and stirred at -78 °C for 1 hour. After that, the reaction mixture was slowly warmed to room temperature and stirring was continued for 2 hours at room temperature. After completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched with saturated sodium bicarbonate (NaHCO3) solution and diluted with ethyl acetate. The organic layer was washed sequentially with saturated sodium bicarbonate solution and saturated saline. The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the crude product 1-tert-butoxycarbonyl-3-pyrrolidinone (4 g, 100% yield), which could be used for subsequent reactions without further purification. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.79-3.75 (m, 4H), 2.58 (t, J = 8.0 Hz, 2H), 1.47 (s, 9H).
Einzelnachweise
[1] NAIRA VIEIRA MACHADO á. O. Enantioselective reduction of heterocyclic ketones with low level of asymmetry using carrots[J]. Biocatalysis and Biotransformation, 2021. DOI:10.1080/10242422.2021.1879795.

N-Boc-3-pyrrolidinone Upstream-Materialien And Downstream Produkte

N-Boc-3-pyrrolidinone Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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