1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-[4-(4-Methoxy-5,6,7,8-tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione

HRID 899808

반응식

HRID 899808 반응식
[NH2:1][CH:2]1[C:11]2[N:10]=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:6]=2[CH2:5][CH2:4][CH2:3]1.[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[CH2:25][CH2:26][CH2:27][CH:28]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:13][O:12][C:7]1[C:6]2[CH2:5][CH2:4][CH2:3][CH:2]([NH:1][CH2:28][CH2:27][CH2:26][CH2:25][N:16]3[C:17](=[O:24])[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:15]3=[O:14])[C:11]=2[N:10]=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 5049666Sodium triacetoxyborohydrideHCID 220186174-Methoxy-5,6,7,8-tetrahydroquinolin-8-amine

생성물 1

HCID 691787902-[4-(4-Methoxy-5,6,7,8-tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione수율 54.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Using General Procedure B: Reaction of 8-amino-4-methoxy-5,6,7,8-tetrahydroquinoline (0.297 g, 1.67 mmol) and 4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (0.371, 1.71 mmol) with NaBH(OAc)3 (0.493 g, 2.33 mmol) in CH2Cl2 (8 mL) for 60 minutes followed by purification of the crude material by column chromatography on silica gel (20:1 CH2Cl—2—CH3OH) provided 0.345 g (54%) of 2-[4-(4-Methoxy-5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione as an off-white solid.

후처리

  1. customfollowed by purification of the crude material by column chromatography on silica gel (20:1 CH2Cl—2—CH3OH)

출처 및 근거

ORD 기록
ord-1dbd991afb534cdaa1e32efa1e4d0f23
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354934B2

연결된 노트

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