2-Bromopropane → Ethyl (1aR,5aR)-2-Isopropyl-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylate

HRID 1623894ノート

反応式

HRID 1623894 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:8][C@H:9]3[CH2:14][C@H:10]3[C:11]=2[NH:12][N:13]=1)=[O:5])[CH3:2].Br[CH:16]([CH3:18])[CH3:17]>CN(C=O)C.CCOC(C)=O>[CH:16]([N:12]1[C:11]2[C@@H:10]3[CH2:14][C@@H:9]3[CH2:8][C:7]=2[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:13]1)([CH3:18])[CH3:17]

参加物

5

反応物 2

HCID 63582-BromopropaneHCID 589068031H-Cyclopropa[4,5]cyclopenta[1,2]pyrazole-3-carboxylic acid, 4,4a,5,5a-tetrahydro-, ethyl ester, (4aR,5aR)-

生成物 1

HCID 86669646Ethyl (1aR,5aR)-2-Isopropyl-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylate収率 59.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

(1aR,5aR)-1a,2,5,5a-Tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid ethyl ester (0.100 g, 0.520 mmol) (from Example 1.4, Step A) was dissolved in anhydrous DMF (5.20 mL). CsCO3 (0.678 g, 2.081 mmol) was added to give a suspension which was stirred at 25° C. for several minutes. 2-Bromopropane (0.098 mL, 1.041 mmol) was added dropwise at 25° C. After stirring for 4 h, the reaction was diluted with EtOAc (50 mL), washed with water (2×10 mL), brine, and dried over MgSO4. The solvent was evaporated under reduced pressure. The oil residue was purified by silica gel column chromatography to give the title compound as an oil (0.073 g). LCMS m/z=235.3 [M+H]+; 1H NMR (400 MHz, CDCl3) ppm 0.29-0.35 (m, 1H), 1.12 (td, J=8.02, 4.93 Hz, 1H), 1.34 (t, J=7.20 Hz, 3H), 1.46 (dd, J=15.16, 6.57 Hz, 6H), 2.04-2.12 (m, 1H), 2.16-2.24 (m, 1H), 2.74-2.82 (m, 1H), 2.90-2.99 (m, 1H), 4.27 (q, J=7.07 Hz, 2H), 5.31-5.43 (m, 1H).

後処理

  1. customto give a suspension which
  2. stirringAfter stirring for 4 h
  3. washwashed with water (2×10 mL), brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated under reduced pressure
  6. customThe oil residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-dcf780a0001648eebbeeeca345f00492
出典データセット
uspto-grants-2014_07
特許番号
US08778950B2

反応ノート

読み込み中…