OTAVA-BB BB7118560909 Chemical Properties

Melting point:

56 °C

Boiling point:

270-290 °C

Density 

1.106

storage temp. 

2-8°C

pka

15.54±0.50(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H11NO2/c1-3-11-8(10)7-6(2)4-5-9-7/h4-5,9H,3H2,1-2H3

InChIKey

FGILMAYWLMWCQA-UHFFFAOYSA-N

SMILES

N1C=CC(C)=C1C(OCC)=O

Safety Information

HS Code 

2933998090

OTAVA-BB BB7118560909 Usage And Synthesis

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 28, p. 1671, 1991 DOI: 10.1002/jhet.5570280705
Tetrahedron Letters, 3, p. 921, 1962

Synthesis

The general procedure for the synthesis of ethyl 3-hydroxy-3-methyl-1-tosylpyrrolidine-2-carboxylate from ethyl 3-hydroxy-3-methyl-1-tosylpyrrolidine-2-carboxylate was as follows: 3-alkylpyrrole derivatives were prepared according to the procedure described in Scheme 1. First, ethyl glycinate 5 was treated with p-toluenesulfonyl chloride (Ts-Cl) to give intermediate 6. Subsequently, intermediate 6 was reacted in the presence of 4-diethylaminobutan-2-one and potassium tert-butanolate (t-BuOK) to produce intermediate 7. Next, intermediate 7 was dehydrated with phosphorus oxychloride (POCl3) to give dihydropyrrole derivative 8. In the presence of sodium ethanolate, the dihydropyrrole derivative was synthesized by an elimination reaction the dihydropyrrole derivative 8 was converted to pyrrole derivative 9. Then, the pyrrole nitrogen was deprotonated using sodium hydride (NaH) and an alkylation reaction was carried out to obtain intermediate 10. finally, the ester group was hydrolyzed by potassium hydroxide (KOH) in aqueous solution in methanol (MeOH), followed by the use of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) to convert the corresponding acid 11 into the target amide products (81), (82) and (83).

References

[1] Patent: WO2009/23272, 2009, A1. Location in patent: Page/Page column 36
[2] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 7, p. 1671 - 1676
[3] Patent: EP2612848, 2013, A1
[4] Patent: WO2009/117421, 2009, A2

OTAVA-BB BB7118560909(3284-47-7)Related Product Information

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• ETHYL 3,4,5-TRIMETHYLPYRROLE-2-CARBOXYLATE
• ETHYL 4-ETHYL-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE
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• 3,4-DIMETHYL-1H-PYRROLE-2-CARBOXYLIC ACID ETHYL ESTER
• ETHYL 5-NITRO-3-PHENYLINDOLE-2-CARBOXYLATE
• 4-(2-CARBOXYETHYL)-3,5-DIMETHYLPYRROLE-2-CARBOXYLIC ACID, ETHYL ETHER
• 5-BROMOMETHYL-3-METHYL-1H-PYRROLE-2,4-DICARBOXYLIC ACID DIETHYL ESTER