HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl morpholine oxide → {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl morpholine oxide | HCID 82029 | — |
| Reactant | {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanol | HCID 86658050 | — |
| Catalyst | HCID 178419074 | HCID 178419074 | — |
| Solvent | Acetonitrile methylene chloride | HCID 21877088 | — |
| Product | {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanone | HCID 86658052 | — |
Reaction Steps
NMO (428 mg, 0.0037 mmol) and TPAP (65 mg, 0.0002 mmol) were added to a stirred solution of {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanol (Intermediate 17, 1.1 g, 0.002 mmol) in CH2Cl2:CH3CN (1:1, 10 mL) 0° C. The mixture was allowed to warm to room temperature with stirring for 12 hours. The solvents were removed, and the residue was purified over a silica gel chromatography column using an ethyl acetate-pet. ether gradient, providing the title compound. Yield: 1 g, (92%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08658641B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-91b0004cf5594e798b719d9770e5bc42 |
| Source note | uspto-grants-2014_02 |