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HRID511539

反应详情

EQUATION

反应方程式

HRID 511539 的结构方程式

REACTANTS

反应物

1
结构：CCOC(=O)C1CC=C(c2ccc(N)c3c(=O)c(C)c[nH]c23)CC1
HCID67254617

未命名化合物

2 次

PRODUCTS

生成物

1
结构：CCOC(=O)[C@H]1CC[C@@H](c2ccc(N)c3c(=O)c(C)c[nH]c32)CC1
HCID178472343

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：[Pd]
催化剂HCID23938

Palladium

Pd

结构：CCO
溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

A mixture of ethyl 4-(5-amino-3-methyl-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate (Compound 304C, 0.270 g, 0.83 mmol) and palladium 10% wt on activated carbon (88.0 mg, 0.083 mmol) in EtOH (2.17 mL) was evacuated and purged with hydrogen (3×) and subsequently stirred under one atmosphere of hydrogen at rt for 16 hrs. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an orange oil. The product was purified by mass directed purification which resolved the cis and trans isomers. Compound 304A, the trans isomer eluted first: 1H NMR (400 MHz, MeOD) δ ppm 1.27 (t, J=7.07 Hz, 3 H) 1.53-1.73 (m, 4 H) 1.79 (d, J=4.29 Hz, 2 H) 2.02 (d, J=0.76 Hz, 3 H) 2.26 (d, J=13.14 Hz, 2 H) 2.70-2.82 (m, 2 H) 4.17 (q, J=7.07 Hz, 2 H) 6.38 (d, J=8.34 Hz, 1 H) 7.12 (d, J=8.34 Hz, 1 H) 7.63 (s, 1 H). MS (ES+): m/z 329.16/329.36 (100/70) [MH+]. HPLC: tR=1.28 min (Micromass TOF: polar—3 min). Compound 304B, the cis isomer eluted after: 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (t, J=7.07 Hz, 3 H) 1.54 (br. s., 1 H) 1.70 (d, J=12.63 Hz, 1 H) 1.87 (br. s., 1 H) 2.02 (d, J=0.51 Hz, 1 H) 2.07 (br. s., 1 H) 2.35-2.45 (m, 1 H) 2.69-2.81 (m, 1 H) 4.12 (q, J=7.07 Hz, 1 H) 6.39 (d, J=8.34 Hz, 1 H) 7.20 (d, J=8.34 Hz, 1 H) 7.64 (d, J=0.76 Hz, 1 H). MS (ES+): m/z 329.14/329.35 (100/70) [MH+]. HPLC: tR=1.30 min (Micromass TOF: polar—3 min).

WORKUP

后处理

  1. customwas evacuated
  2. custompurged with hydrogen (3×)
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo to an orange oil
  5. customThe product was purified by mass
  6. custompurification which
  7. washCompound 304A, the trans isomer eluted first
  8. customHPLC: tR=1.28 min (Micromass TOF: polar—3 min)
  9. washCompound 304B, the cis isomer eluted after: 1H NMR (400 MHz, CDCl3) δ ppm 1.25 (t, J=7.07 Hz, 3 H) 1.54 (br. s., 1 H) 1.70 (d, J=12.63 Hz, 1 H) 1.87 (br. s., 1 H) 2.02 (d, J=0.51 Hz, 1 H) 2.07 (br. s., 1 H) 2.35-2.45 (m, 1 H) 2.69-2.81 (m, 1 H) 4.12 (q, J=7.07 Hz, 1 H) 6.39 (d, J=8.34 Hz, 1 H) 7.20 (d, J=8.34 Hz, 1 H) 7.64 (d, J=0.76 Hz, 1 H)
  10. customHPLC: tR=1.30 min (Micromass TOF: polar—3 min)