Ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate → HCID 178472336, 화합물

HRID 604665노트

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HRID 604665 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

4

반응물 1

HCID 67057759Ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate

생성물 1

HCID 178472336HCID 178472336, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate (270 mg, 0.955-mmoL) in EtOAc (15 mL) was added 10% Pd/C (45 mg). The reaction was put under an atmosphere of H2 (balloon) and stirred vigorously at room temperature. After 30 min, the catalyst was removed by filtration, and the filtrate was concentrated to afford a mixture of cis and trans products. The desired trans isomer was separated by flash chromatography on silica gel (0 to 10% EtOAc/hexanes) to afford ethyl trans-4-(3-chloro-4-fluorophenyl)cyclohexanecarboxylate. Rf=0.25 (5% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3): δ 7.21 (d, J=7.3 Hz, 1H), 7.02-7.06 (m, 2H), 4-14 (q, J=7.1 Hz, 2H), 2.48 (m, 1H), 2.32 (m, 1H), 2.08-2.12 (m, 2H), 1.91-1.98 (m, 2H), 1.53-1.67 (m, 2H), 1.37-1.46 (m, 2H), 1.27 (t, J=7.1 Hz, 3H).

후처리

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto afford
  4. additiona mixture of cis and trans products
  5. customThe desired trans isomer was separated by flash chromatography on silica gel (0 to 10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-7623c83a420a4f80a1d1061b4b24a641
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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