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).

引用

页码：644 / 648

页数：5

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