4-Methoxy cinnamic acid → (S)-Benzyl N-(4-Methoxycinnamoyl)pipecolate

HRID 1377881

반응식

HRID 1377881 반응식
[NH:1]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:2]1[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([CH:23]=[CH:24][C:25](O)=[O:26])=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([CH:23]=[CH:24][C:25]([N:1]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:2]2[C:3]([O:5][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:4])=[O:26])=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 132454-Methoxy cinnamic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12436231(S)-Benzyl piperidine-2-carboxylate

생성물 1

HCID 86746605(S)-Benzyl N-(4-Methoxycinnamoyl)pipecolate수율 65%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 145 mg (0.37 mmol) of (S)-Benzyl pipecolate salt (14) (described in Example 1) in 8.0 mL of methylene chloride was added 102 mg (0.57 mmol) of 4-methoxycinnamic acid, 107 mg (0.55 mmol) of 1-(3-di-methylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and 130 μL (0.74 mmol) of diisopropylethylamine. The resulting solution was stirred at ambient temperature for 12 h and was then concentrated under reduced pressure. Flash chromatography (elution with 1:1 ethyl acetate-hexane) gave 91 mg (65%) of the amide (8) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ7.66 (d), 7.50 (d), 7.35 (m), 6.90 (d), 6.82 (d), 6.63 (d), 5.55 (d), 5.20 (br s), 4.86 (br s), 4.67 (br d) 4.03 (br d), 3.83 (s), 3.37 (dr), 2.78 (dr) 2.33 (br d), 1.74 (m), 1.43 (m). Rf 0.40 (1:1 ether-hexane).

후처리

  1. concentrationwas then concentrated under reduced pressure
  2. washFlash chromatography (elution with 1:1 ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-10c962e0a71d4594a5425a6dc3a5e433
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665774

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