Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 1,1,1-Trifluoro-2-iodoethane | HCID 67709 | — |
| Reactant | HCID 58109237 | HCID 58109237 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 66857740 | HCID 66857740 | 58% |
Reaction Steps
A mixture of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-hydroxyphenyl)ethyl)-1,3-oxazinan-2-one (700 mg, 1.97 mmol), CF3CH2I (621 mg, 2.96 mmol) and CsF (360 mg, 2.37 mmol) in DMSO (10 mL) was heated under 120° C. overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparative TLC to give (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-1-(4-(2,2,2-trifluoroethoxy)phenyl)ethyl)-1,3-oxazinan-2-one (500 mg, 58%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08575156B2 |
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| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-346375903a7b45d793644412a74b531c |
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| Source note | uspto-grants-2013_11 |
|---|
