Benzyl trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1-carboxylate → tert-Butyl (trans(+/-)-3-{[tert-butyl(dimethyl)silyl]oxy}piperidin-4-yl)carbamate
反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11][C@H:10]1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[Si:26]([O:25][C@H:10]1[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][NH:12][CH2:11]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]参加物
4
実験手順
A mixture of (+/−)-(3R,4R)-benzyl 4-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate (13 g, 28.0 mmol) and Pd/C (5% on carbon, 1.786 g, 0.839 mmol) in methanol (250 mL) was hydrogenated at 30 psi overnight. The mixture was filtered through Celite and the filtrate was concentrated in vacuo and further dried under high vacuum at 40° C. overnight. The crude product was used without purification. (+/−)-tert-butyl ((3R,4R)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)carbamate (8.8 g, 26.6 mmol, 95% yield) was obtained as a white solid.
後処理
- customwas hydrogenated at 30 psi overnight
- filtrationThe mixture was filtered through Celite
- concentrationthe filtrate was concentrated in vacuo
- customfurther dried under high vacuum at 40° C. overnight
- customThe crude product was used without purification
出典と根拠
- ORDレコード
- ord-c235ee6d722841838ed611ea6b6fe686
- 出典データセット
- uspto-grants-2015_01
- 特許番号
- US08940736B2
反応ノート
読み込み中…