METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE Chemical Properties

Melting point:

62-64 °C

Boiling point:

132-142 °C(Press: 0.45 Torr)

Density 

1.204

refractive index 

1.465

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

15.31±0.40(Predicted)

color 

Pale Beige to Pale Brown

InChI

InChI=1S/C6H9NO3/c1-10-6(9)4-2-5(8)7-3-4/h4H,2-3H2,1H3,(H,7,8)

InChIKey

FJRTVLWHONLTLA-UHFFFAOYSA-N

SMILES

N1C(=O)CC(C(OC)=O)C1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE Usage And Synthesis

Uses

Methyl 5-Oxopyrrolidine-3-carboxylate has been used as a reactant in the synthesis of tert-butyloxycarbonyl protected 4,5-methano-β-proline.

Synthesis

General procedure for the synthesis of methyl 5-oxopyrrolidine-3-carboxylate from methyl 1-(benzyloxy)-5-oxopyrrolidine-3-carboxylate: to an autoclave was added methyl 1-(benzyloxy)-5-oxopyrrolidine-3-carboxylate (51.0 g, 0.205 mol), 10% Pd-C catalyst (9.0 g) and methanol (400 mL). The reaction mixture was stirred vigorously at room temperature under 50 atm hydrogen pressure for 24 hours. Upon completion of the reaction, the suspension was filtered to remove the catalyst and the catalyst residue was washed with methanol (2 x 100 mL). The filtrate and washings were combined and the solvent was removed by distillation under reduced pressure to afford the colorless oily product methyl 5-oxopyrrolidine-3-carboxylate (29.2 g, 100% yield), which crystallized upon standing. The melting point of the product was 55-58 °C (literature value 10b 61-62 °C). Mass spectrum (m/z, CI): 287 (M2H+), 144 (MH+). Elemental analysis (C6H9NO3) Calculated values: C 50.35, H 6.34, N 9.79; measured values: C 50.13, H 6.47, N 10.02.1H NMR (500 MHz, DMSO-d6) δ 7.67 (s, 1H), 3.64 (s, 3H), 3.46 (t, J=11.1Hz, 1H), 3.39- 3.31 (m, 2H), 2.43-2.28 (m, 2H).13C NMR (126 MHz, DMSO-d6) δ 175.4,174.0,52.4,44.0,38.4,33.4.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3312 - 3315

METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE(35309-35-4)Related Product Information

• MFCD22689490
• ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate
• ethyl 1-(2,5-dioxopyrrolidin-3-yl)piperidine-4-carboxylate
• ETHYL 1-ETHYL-4,5-DIOXOPYRROLIDINE-3-CARBOXYLATE, 97
• Methyl 1-Benzyl-5-oxopyrrolidine-3-carboxylate
• Methyl 5-Oxo-1-phenylpyrrolidine-3-carboxylate
• 1-METHYL-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID
• ETHYL 1-(2-FURYLMETHYL)-4,5-DIOXOPYRROLIDINE-3-CARBOXYLATE
• ETHYL 1-(TERT-BUTYL)-4,5-DIOXOPYRROLIDINE-3-CARBOXYLATE
• 2-(DANSYLSULFONAMIDO)ETHYL-3-(N-SULFOSUCCINIMIDYLCARBOXY)ETHYL DISULFIDE, SODIUM SALT
• METHYL 1-([3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]AMINO)-5-OXO-3-PYRROLIDINECARBOXYLATE
• 2-[N2-(4-AZIDO-2,3,5,6-TETRAFLUOROBENZOYL)-N6-(6-BIOTINAMIDOCAPROYL)-L-LYSINYL]ETHYL 2'- (N-SULFOSUCCINIMIDYLCARBOXY)ETHYL DISULFIDE, SODIUM SALT
• METHYL 5-OXO-1-(2-THIENYLMETHYL)PYRROLIDINE-3-CARBOXYLATE
• METHYL 1-(4-BROMOPHENYL)-5-OXO-3-PYRROLIDINECARBOXYLATE
• 2-[(N2-[N6-(4-AZIDO-2,3,5,6-TETRAFLUOROBENZOYL)-6-AMINOCAPROYL]-N6-(6-BIOTINAMIDOCAPROYL)-L-LYSINYLAMIDO)] ETHYL 2-(N-SULFOSUCCINIMYDYLCARBOXY)ETHYL DISULFIDE, SODIUM SALT
• METHYL 1-(4-ETHYLPHENYL)-5-OXOPYRROLIDINE-3-CARBOXYLATE
• METHYL 1-[2-(1H-INDOL-3-YL)ETHYL]-5-OXO-3-PYRROLIDINECARBOXYLATE
• METHYL 1-CYCLOHEXYL-5-OXO-3-PYRROLIDINECARBOXYLATE