Diisopropylethylamine → (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one
反応式
[CH2:1]([O:4][NH:5][C@@H:6]1[CH:11]=[CH:10][C@@H:9]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[NH:8][CH2:7]1)[CH:2]=[CH2:3].C(N(C(C)C)C(C)C)C.[C:30](=O)(OC(Cl)(Cl)Cl)[O:31]C(Cl)(Cl)Cl>C(#N)C>[CH2:1]([O:4][N:5]1[C:30](=[O:31])[N:8]2[CH2:7][C@H:6]1[CH:11]=[CH:10][C@H:9]2[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH:2]=[CH2:3]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
To a stirred solution of O-allyl-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamine (Intermediate 128, 2.0 g, 6.70 mmol) in acetonitrile (560 mL), N-ethyl-N-isopropylpropan-2-amine (4.67 ml, 26.80 mmol) was added. Bis(trichloromethyl) carbonate (0.795 g, 2.68 mmol) dissolved in 40 mL CH3CN was added via a syringe pump (at a rate 0.1 ml/min) at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. It was then allowed to stir at room temperature overnight. The mixture was then concentrated and diluted with EtOAc (50 mL). The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column (12 g, 0-25% Hex/EA) to give the desired product as a colorless oil (1.64 g).
後処理
- additionwas added via a syringe pump (at a rate 0.1 ml/min) at 0° C
- stirringto stir at room temperature overnight
- concentrationThe mixture was then concentrated
- additiondiluted with EtOAc (50 mL)
- washThe organic layer was washed with water, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel column (12 g, 0-25% Hex/EA)
出典と根拠
- ORDレコード
- ord-f86c167064fd4865b7141b679157ba25
- 出典データセット
- uspto-grants-2016_04
- 特許番号
- US09309245B2
反応ノート
読み込み中…