反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8]1.[CH3:17][O:18][NH:19][C:20](=O)[O:21]C1C=CC([N+]([O-])=O)=CC=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH3:17][O:18][NH:19][C:20]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][CH:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:21]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
A solution of 2-pyridin-2-yl-1,2,3,4-tetrahydroquinoline (0.723 g, 3.44 mmol) in methylene chloride (10.3 mL) was treated with 4-nitrophenyl methoxycarbamate (0.948 g, 4.47 mmol) (Org. Process Res. Dev. 2012, 16, 109-116) followed by the dropwise addition of N,N-diisopropylethylamine (1.20 mL, 6.88 mmol), and the resulting mixture was stirred at room temperature for 1.5 h. The reaction mixture was then poured over water (25 mL) and saturated sodium bicarbonate (25 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to give a crude oily solid. Purification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes [the ethyl acetate contained 5% methanol]) gave the desired product (0.923 g, 95%) as a racemic mixture. LCMS calculated for C16H18N3O2 (M+H)+: m/z=284.1. found: 284.0.
後処理
- extractionextracted with dichloromethane (2×50 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give a crude oily solid
- customPurification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes [the ethyl acetate
出典と根拠
- ORDレコード
- ord-ab994f55efbd452aa72be3d56fa76a88
- 出典データセット
- uspto-grants-2016_01
- 特許番号
- US09227985B2
関連ノート
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