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Phenylmethyl 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-8-azaspiro[4.5]decane-8-carboxylate → 1,1-Dimethylethyl (3-hydroxy-8-azaspiro[4.5]dec-2-yl)carbamate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Phenylmethyl 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-8-azaspiro[4.5]decane-8-carboxylate | HCID 69054060 | — |
| 触媒 | Palladium hydroxide | HCID 9942167 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 生成物 | 1,1-Dimethylethyl (3-hydroxy-8-azaspiro[4.5]dec-2-yl)carbamate | HCID 76580869 | 31% |
反応手順
To a solution of phenylmethyl 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (˜3.1 g, 7.65 mmol) in EtOH (38 mL) was added Pd(OH)2 (1.5 g, 50 wt %). The solution was hydrogenated using a Parr Shaker at 50 psi. After 2 h, the solution was filtered through Celite®, concentrated and purified by column chromatography (silica, 15% MeOH in DCM (1% NH4OH)) yielding the title compound (618 mg, 31%-2 steps) as a yellow oil: LCMS (ES) m/e 272 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07592334B2 |
| 出典データセット | uspto-grants-2009_09 |
| ORD ID | ord-08d2255fd3c7486f82e7d40cbf642e9e |
| 出典メモ | uspto-grants-2009_09 |