HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl morpholine oxide → {5-([{tert-butyl(diphenyl)silyl]oxy}methyl)-3-chloro-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2-fluorophenyl}(pyridin-2-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl morpholine oxide | HCID 82029 | — |
| Reactant | {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-3-chloro-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2-fluorophenyl}(pyridin-2-yl)methanol | HCID 86717851 | — |
| Catalyst | HCID 178419074 | HCID 178419074 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | {5-([{tert-butyl(diphenyl)silyl]oxy}methyl)-3-chloro-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2-fluorophenyl}(pyridin-2-yl)methanone | HCID 87399248 | — |
Reaction Steps
To the solution of {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-3-chloro-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2-fluorophenyl}(pyridin-2-yl)methanol (Intermediate 62, 100 mg, 0.165 mmol) in anhydrous DCM (5 mL) was added NMO (37 mg, 0.323 mmol) and TPAP (0.1 eq) at 0° C. and the mixture was allowed to stir for 1 hour at room temperature. The reaction mixture was filtered and the solvents were removed under vacuum and the residue was purified over silica gel chromatography column using ethyl acetate-pet. ether gradient to give product as a solid. Yield: 90 mg, (90%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09040528B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-ebd703ea07ff47aea6be66652bcd49f5 |
| Source note | uspto-grants-2015_05 |