HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetaldehyde → Benzyl 6-(1-hydroxyethyl)-6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetaldehyde | HCID 177 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | Benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate | HCID 15136304 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Benzyl 6-(1-hydroxyethyl)-6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate | HCID 15136305 | — |
Reaction Steps
Benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate is converted to its enolate derivative with lithium diisopropylamide in anhydrous THF at -78° as described in the previous example. To this solution is added 10 equivalents of acetaldehyde. Workup as described in example 16 yields benzyl 6-(1-hydroxyethyl)-6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05021566 |
| Source dataset | uspto-grants-1991_06 |
| ORD ID | ord-c4c933fa616f4b589250c5eab2867ea0 |
| Source note | uspto-grants-1991_06 |