関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | 1,4-Dioxane | HCID 31275 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Carbonic acid, 1,1-dimethylethyl 2,5-dioxo-1-pyrrolidinyl ester | HCID 83168 | — |
| 反応物 | tert-butyl ((3S,4S,5R)-1-(3-((tert-butoxycarbonyl)amino)pyridin-4-yl)-4-cyano-5-methylpiperidin-3-yl)carbamate | HCID 86705276 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | tert-butyl (3S,4S,5R)-1-(3-aminopyridin-4-yl)-4-cyano-5-methylpiperidin-3-ylcarbamate | HCID 86705279 | 100% |
反応手順
Tert-butyl ((3S,4S,5R)-1-(3-((tert-butoxycarbonyl)amino)pyridin-4-yl)-4-cyano-5-methylpiperidin-3-yl)carbamate (1.0 equiv.) was treated with 4 M HCl in dioxane (30.0 equiv.) at rt for 1 hour. The volatiles were removed in vacuo and the solid was pumped on for 5 minutes on the high vac. To the residue was added CH2Cl2 (0.05 M), DIEA (5.0 equiv.) and Boc-OSu (1.6 equiv.). The solution was left stirring at rt for 1 hr. The volatiles were removed in vacuo and the residue was partitioned between EtOAc and H2O. The organic layer was washed with Na2CO3(sat), NaCl(sat), dried over MgSO4, filtered, concentrated to yield tert-butyl (3S,4S,5R)-1-(3-aminopyridin-4-yl)-4-cyano-5-methylpiperidin-3-ylcarbamate in 100% yield. LC/MS (m/z)=332.1 (MH+), Rt=0.59 min.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09173883B2 |
|---|
| 出典データセット | uspto-grants-2015_11 |
|---|
| ORD ID | ord-68cbbaa1123f406d9497c662a3afa2bc |
|---|
| 出典メモ | uspto-grants-2015_11 |
|---|
