1-N-Cbz-3-pyrrolidinone Chemical Properties

Melting point:

45-47°C

Boiling point:

370.2±42.0 °C(Predicted)

Density 

1.1897 g/mL at 25 °C

refractive index 

n20/D 1.5410

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

-1.84±0.20(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C12H13NO3/c14-11-6-7-13(8-11)12(15)16-9-10-4-2-1-3-5-10/h1-5H,6-9H2

InChIKey

LMHWEUQNJRXMCD-UHFFFAOYSA-N

SMILES

N1(C(OCC2=CC=CC=C2)=O)CCC(=O)C1

CAS DataBase Reference

130312-02-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-40

Safety Statements 

23-24/25-36/37

WGK Germany 

2

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

1-N-Cbz-3-pyrrolidinone Usage And Synthesis

Chemical Properties

Light yellow solid

Synthesis

General procedure for the synthesis of N-Cbz-3-pyrrolidinone from N-CBZ-3-hydroxypyrrolidine: intermediate 6.iii (1.10 g) was dissolved in dichloromethane (DCM, 8 mL) and cooled to 0 °C. Under stirring, N,N-diisopropylethylamine (DIPEA, 2.5 mL) was added slowly and dropwise, followed by a solution of sulfur trioxide pyridine complex (1.79 g) in dimethyl sulfoxide (DMSO, 6.5 mL). The reaction mixture was stirred continuously at 0 °C for 1 h, after which the reaction was quenched by the addition of water (6 mL). The aqueous phase was extracted with a solvent mixture of ether/hexane (1:1, 3 × 5 mL) and the organic phases were combined. After the organic phase was concentrated under vacuum, the residue obtained was solubilized with a solvent mixture of ether/hexane (1:1) and purified by silica gel column chromatography (n-hexane/ethyl acetate, 5:5) to give 1.05 g (96% yield) of the light yellow oily product N-Cbz-3-pyrrolidinone. The product was characterized by 1H NMR (DMSO-d6; δ ppm): 2.48-2.61 (2H, m); 3.61-3.80 (4H, m); 5.09 (2H, s); 7.27-7.41 (5H, m).

References

[1] Patent: US2009/247578, 2009, A1. Location in patent: Page/Page column 14
[2] Patent: WO2008/56335, 2008, A1. Location in patent: Page/Page column 34
[3] Patent: WO2014/32, 2014, A1. Location in patent: Page/Page column 51; 52
[4] Chemical Communications, 2007, # 21, p. 2136 - 2138
[5] Patent: WO2017/216726, 2017, A1. Location in patent: Page/Page column 581

1-N-Cbz-3-pyrrolidinone(130312-02-6)Related Product Information

• N-Vinyl-2-pyrrolidone
• 2-Pyrrolidinone
• Pyrrolidine
• 3-Pyrrolidinone
• Polyvinylpyrrolidone
• Crospovidone
• N-Methyl-2-pyrrolidone
• Ethyl N-Cbz-4-Oxopyrrolidine-3-carboxylate
• METHYL-2-PYRROLIDONE
• 4,4-PENTAMETHYLENE-2-PYRROLIDINONE
• 1-CBZ-3-PYRROLIDINONE,N-CBZ-3-PYRROLIDINONE
• 4,4-PENTAMETHYLENE-2-PYRROLIDINONE
• 4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]-2-PYRROLIDINONE
• 4-PHENYL-2-PYRROLIDINONE
• Pyrrole
• 2-Pyrrolidineacetic acid, 3-oxo-1-[(phenylmethoxy)carbonyl]-, ethyl ester
• N-CBZ-4-OXO-D-PROLINE
• N-CBZ-2-AZABICYCLO[2.2.1]HEPTAN-7-ONE