Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2,6-Lutidine | HCID 7937 | — |
| Reactant | Trimethylsilyl triflate | HCID 65367 | — |
| Reactant | HCID 86708546 | HCID 86708546 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86708545 | HCID 86708545 | 33.1% |
Reaction Steps
(S)-tert-butyl (2-chloro-5-cyano-3-(3,3-dimethylhexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl)phenyl)carbamate (87 mg, 0.207 mmol) was taken up in DCM (2 mL) and cooled to 0° C. 2,6-Lutidine (0.072 mL, 0.620 mmol) was added, followed by dropwise addition of trimethylsilyl trifluoromethanesulfonate (0.112 mL, 0.620 mmol). The reaction was stirred at 0° C. for 30 min, then warmed to room temperature and stirred for 30 min. The solvent was removed in vacuo and the material was purified by flash column chromatography, eluting with 0-2% (2N NH3/MeOH)/DCM. (S)-3-amino-4-chloro-5-(3,3-dimethylhexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl)benzonitrile (22 mg) was obtained as a yellow glass.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09273057B2 |
|---|
| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-d9742883cb2b467cb953d50b73ced897 |
|---|
| Source note | uspto-grants-2016_03 |
|---|