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Methanol → (R,R)-N-(4-phenyl-2-butyl)-1-(3-methoxyphenyl)ethylamine

HRID 322578
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HRID 322578 반응식
[C:1]1([CH2:7][CH2:8][C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C@H:20]([NH2:22])[CH3:21])[CH:17]=[CH:18][CH:19]=1.C([BH3-])#N.[Na+].CO>C(Cl)(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:1]1([CH2:7][CH2:8][C@H:9]([NH:22][C@@H:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)[CH3:21])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH2:7][CH2:8][C@H:9]([NH:22][C@H:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)[CH3:21])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 887MethanolHCID 17355Benzyl acetoneHCID 5003444Sodium cyanoborohydrideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamine

생성물 2

HCID 28104230(R,R)-N-(4-phenyl-2-butyl)-1-(3-methoxyphenyl)ethylamineHCID 28104232(S,R)-N-(4-pbenyl-2-butyl)-1-(3-methoxyphenyl)ethylamine

시약·촉매·용매

2
HCID 11026Titanium isopropoxide촉매HCID 6212Chloroform용매

실험 절차

In a similar fashion an equal molar amount of 4-phenyl-2-butanone (Aldrich Chemical Co.), (R)-1-(3-methoxyphenyl)ethylamine and 1.25 equivalents titanium(IV) isopropoxide were mixed and the intermediate imine reduced with ethanolic sodium cyanoborohydride. Work-up and repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded (R,R)-N-(4-phenyl-2-butyl)-1-(3-methoxyphenyl)ethylamine, 21D [m/z (rel. int.) 283 (M+, 4), 268 (13), 178 (45), 135 (100), 105 (15), 91 (43), 77 (11)] and (S,R)- N-(4-pbenyl-2-butyl)-1-(3-methoxyphenyl)ethylamine, 21E.

출처 및 근거

ORD 기록
ord-aed6f5fe9e0d433f8dbe9df82f9b2ae9
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211244B1

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