Potassium Carbonate → 4-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}butyric acid methyl ester

HRID 1097289노트

반응식

HRID 1097289 반응식
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C([O-])([O-])=O.[K+].[K+].I[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:33](=[O:34])[CH:32]2[CH:27]([CH:28]=[CH:29][CH:30]=[CH:31]2)[C:26]1=[O:35]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[C:33](=[O:34])[CH:32]3[CH:27]([CH:28]=[CH:29][CH:30]=[CH:31]3)[C:26]2=[O:35])[CH2:9][CH2:8]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 21462751Methyl 4-(piperidin-4-yl)butanoateHCID 668110452-(4-Iodobutyl)-3a,7a-dihydroisoindole-1,3-dione

생성물 1

HCID 668112194-{1-[4-(1,3-Dioxo-1,3,3a,7a-tetrahydroisoindol-2-yl)butyl]piperidin-4-yl}butyric acid methyl ester수율 40%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a suspension of 2 (1.96 g, 8.86 mmol), K2CO3 (2.82 g, 17.72 mmol) and acetone (100 mL) was added 2-(4-iodobutyl)-3a,7a-dihydroisoindole-1,3-dione (2.93 g, 8.86 mmol). The newly formed suspension was stirred at ambient temperature for 48 hours. The solid was vacuum filtered and the filtrate was concentrated under vacuum. The resulting residue was subjected to column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the desired product 3 (0.63 g, 40%) as a white solid: 1H NMR (500 MHz; CDCl3) δ 1.16-1.28 (m, 3H), 1.65 (m, 2H), 1.60-1.72 (m, 4H), 1.86 (m, 2H), 2.26 (t, 2H), 2.32 (t, 2H), 2.88 (d, 2H) 3.64 (s, 3H), 3.70 (t, 2H), 7.68 (d, 2H), 7.72 (d, 2H).

후처리

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under vacuum
  3. washeluting with 0-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-bd9a0a83445a4034b9c4bff40b2be306
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143256B2

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