A scalable synthesis of (R)-3,5-dihydro-4H-dinaphth[2,1-c:12-e]azepine

被引：20
|
作者：
Ikunaka, M
Maruoka, K
Okuda, Y
Ooi, T
机构：
[1] Nagase & Co Ltd, Res & Dev Ctr, Second Labs, Nishi Ku, Kobe, Hyogo 6512241, Japan
[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
[3] Nagase ChemteX Corp, BioFine Chem Div, Prod Dev Sect 4, Nishi Ku, Kobe, Hyogo 6512241, Japan
来源：
ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2003年 / 7卷 / 05期
关键词：
D O I：
10.1021/op034067t
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Environmentally benign scalable procedures are developed to supply enantiomerically pure (R)-3,5-dihydro-4H-dinaphth[2,1-c:1'2'-e]azepine 1 as its hydrogen oxalate salt in a five-step overall yield of 41%, which consist of the following: (1) his O-triflation of (R)-1,1'-bi-2-naphthol 8 [(CF3SO2)(2)O, pyridine, PhMe; quantitative yield]; (2) Kumada's cross-coupling [MeMgI, NiCl2(dppp), tent-BuOMe; 96% yield]; (3) radical bromination [N-bromosuccinimide, 2,2'-azobisisobutyronitrile, cyclohexane; 54% yield]; (4) cyclization [allylamine, Et3N, THF, 86%]; (5) N-deallylation [1,3-dimethylbarbituric acid, Pd(OAc)(2), Ph3P, PhMe] followed by crystalline salt formation with oxalic acid (overall 92% yield).
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页码：644 / 648
页数：5
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