Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | Cyclohexanecarboxamide, 4-methylene- | HCID 57762762 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86723565 | HCID 86723565 | 35.7% |
Reaction Steps
Compound 8-3 (9.5 g, 0.068 mol) was dissolved in 300 mL of THF, and lithium aluminium hydride (2.62 g, 0.069 mol) was added slowly at −10° C. After the addition, reacted at room temperature for 2 hours, and added 5 mL of water after completion of the reaction of raw materials, suction filtered through Celite and the filtrate was concentrated to give an oil. The obtained oil and triethylamine (10.7 mL, 0.075 mol) were dissolved in 100 mL of DCM, and added dropwise benzyl chloroformate (11.6 g, 0.068 mol) slowly at −10° C., then further reacted for 2 hours at room temperature after the addition was completed. The reaction mixture was washed with 100 mL of water and 100 mL of saturated brine once respectively, dried and concentrated and purified by column chromatography (petroleum ether/ethyl acetate=10:1) to give Compound 8-4 as a white solid (6.3 g, yield 35.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09365499B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-f2caf040569a4134b7b4fc156e03985e |
|---|
| Source note | uspto-grants-2016_06 |
|---|