Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 76831232 | HCID 76831232 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 76831082 | HCID 76831082 | 92% |
Reaction Steps
To a suspension of N-[(1SR,2RS)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxymethyl-cyclopropyl]-2-chloro-acetamide (intermediate B9A) (495 mg, 1.47 mmol) in tert-butanol (6 ml) at 23° C. was added potassium tert-butoxide (KOBut) (550 mg, 4.9 mmol) in one portion [exothermic] and the mixture was stirred at 23° C. for 19 h. Poured into 1 M HCl, extracted with ethyl acetate, washed organic layer with brine, dried over sodium sulfate. Removal of the solvent in vacuum left an orange oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound as a white gum (405 mg, 92%). MS (ISP): m/z=300.1 [(M+H)−] and 302.2 [(M+2+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08673894B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-f1acd06d7f6c4fc6a5f94578863712b0 |
|---|
| Source note | uspto-grants-2014_03 |
|---|