HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → (1S,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-enecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Acetylacetone | HCID 31261 | — |
| Reactant | 1-Iodopropane | HCID 33643 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | (1R,4S)-4-Aminocyclopent-2-ene-1-carboxylic acid | HCID 2734525 | — |
| Reactant | (1R,4S)-methyl 4-aminocyclopent-2-enecarboxylate | HCID 11412436 | — |
| Reactant | (1R,4S)-methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-enecarboxylate | HCID 59700297 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (1S,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-enecarboxylic acid | HCID 11402372 | — |
Reaction Steps
Here, (1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid is converted into the corresponding methyl ester by treatment with thionyl chloride in methanol. Methyl (1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-ene-1-carboxylate is then synthesized by reacting the (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate methyl ester with 2,4-pentanedione in the presence of DIEA. The following alkylation of methyl (1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-ene-1-carboxylate with iodopropane is carried out using lithium bis-(trimethylsilyl)amide as a base. The resulting alkylated product is then hydrolyzed to form the (1S,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-ene-1-carboxylic acid 4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07361765B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-24fa5dbe5d424207acaf7974f4fb184d |
| Source note | uspto-grants-2008_04 |