Ikunaka, Masaya published the artcileA Scalable Synthesis of (R)-3,5-Dihydro-4H-dinaphth[2,1-c:1’2′-e]azepine, SDS of cas: 126613-06-7, the publication is Organic Process Research & Development (2003), 7(5), 644-648, database is CAplus.
Environmentally benign scalable procedures are developed to supply enantiomerically pure (R)-3,5-dihydro-4H-dinaphth[2,1-c:1’2′-e]azepine as its hydrogen oxalate salt in a five-step overall yield of 41%, which consist of the following: (1) bis O-triflation of (R)-1,1′-bi-2-naphthol [(CF3SO2)2O, pyridine, PhMe; quant. yield]; (2) Kumada’s cross-coupling [MeMgI, NiCl2(dppp), tert-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).
Organic Process Research & Development published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C22H12F6O6S2, SDS of cas: 126613-06-7.
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