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

HRID 1623894노트

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HRID 1623894 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-dcf780a0001648eebbeeeca345f00492
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778950B2

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