N-Boc-3-pyrrolidinone Chemical Properties

Melting point:

34-38 °C (lit.)

Boiling point:

270.9±33.0 °C(Predicted)

Density 

1.133±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Dichloromethane, Ethyl Acetate, Methanol

pka

-1.79±0.20(Predicted)

form 

Low Melting Solid

color 

White to yellow to orange

Water Solubility 

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 DataBase Reference

101385-93-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41-36/37/38-20/21/22

Safety Statements 

26-36/37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

N-Boc-3-pyrrolidinone Usage And Synthesis

Description

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].

Chemical Properties

Brown Oil

Uses

In the Synthesis and antibacterial evaluation of a novel series of rifabutin-like spirorifamycins 1-Boc-3-pyrrolidinone is used.

Uses

Used in a study of asymmetric hydrogen-transfer bioreduction of ketones with Leifsonia alcohol dehydrogenase.

Synthesis

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).

References

[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(101385-93-7)Related Product Information

• 2-Pyrrolidinone
• tert-Butanol
• Crospovidone
• 3-Pyrrolidinone
• Polyvinylpyrrolidone
• tert-Butyl acetate
• N-Methyl-2-pyrrolidone
• N-Vinyl-2-pyrrolidone
• tert-Butyl peroxyacetate
• 1-N-Boc-3-hydroxyazetidine
• METHYL-2-PYRROLIDONE
• BOC-3-FLUORO-4-OXOPYRROLIDINE
• 1-Boc-3-cyano-4-oxopyrrolidine
• 1-(TERT-BUTOXYCARBONYL)-4-OXOPYRROLIDINE-2-CARBOXYLIC ACID
• N-Boc-4-oxo-L-proline
• N-BOC-2-AZABICYCLO[2.2.1]HEPTAN-7-ONE
• 1-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate
• BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER