HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → Benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Benzyl 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]-8-carboxylate | HCID 74394144 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate | HCID 51030438 | — |
Reaction Conditions
| Temperature | 4 °C |
|---|
Reaction Steps
To a cold (0° C.) solution of EXAMPLE 84A (3.5 g) in tetrahydrofuran (40 mL) was added boron trifluoride diethyl ether complex (0.82 mL). The mixture was stirred at 3-5° C. for 3 hours. Aqueous saturated NaHCO3 was added, followed by ethyl acetate (200 mL). The organic layer was separated, washed with water (twice) and concentrated to dryness. Toluene was added and the mixture was concentrated under vacuum to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889675B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-19222742187240558bbb5ec36574dc5c |
| Source note | uspto-grants-2014_11 |