Dichloromethane → Tert-butyl 5-cyano-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate
反応式
C(Cl)Cl.[C:4]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([N:10]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8]1)[CH2:14]2)(=O)[NH2:5].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>CCOC(C)=O>[C:4]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([N:10]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8]1)[CH2:14]2)#[N:5]参加物
実験手順
A 50 mL RB flask fitted with magnetic stirrer was charged with 5 mL of DCM and tert-butyl 5-carbamoyl-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate, Intermediate-11 (0.8 g, 2.8 mmol). Under N2 atm, triethyl amine (1.15 g, 11.4 mmol) and trifluoroacetic anhydride (2.4 g, 11.4 mmol) was added and stirred for 6 hr. After completion of the reaction (reaction was monitored by TLC), reaction mixture was quenched with KHSO4 solution and extracted with DCM (50 ml×3). The organic layer was washed with saturated sodium bi carbonate solution followed by brine solution. Finally the reaction mixture was dried over anhydrous sodium sulfate and concentrated to give crude Intermediate-13, which was subjected to column chromatogram (10% EtOAc in PE) as a off-white solid (0.5 g, yield=70%).
後処理
- customA 50 mL RB flask fitted with magnetic stirrer
- customAfter completion of the reaction (reaction was monitored by TLC), reaction mixture
- customwas quenched with KHSO4 solution
- extractionextracted with DCM (50 ml×3)
- washThe organic layer was washed with saturated sodium bi carbonate solution
- dry with materialFinally the reaction mixture was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customto give crude Intermediate-13, which
出典と根拠
- ORDレコード
- ord-7702bddefc004d3886d4ca6cc06a72ad
- 出典データセット
- uspto-grants-2016_04
- 特許番号
- US09303016B2
反応ノート
読み込み中…