(R)-(4-bromophenyl)(phenyl)methanamine; (R)-(4-bromophenyl)(phenyl)methylamine -Drug Synthesis Database

【结构式】

【分子编号】38291

【品名】(R)-(4-bromophenyl)(phenyl)methanamine; (R)-(4-bromophenyl)(phenyl)methylamine

【CA登记号】

【分子式】C₁₃H₁₂BrN

【分子量】262.14902

【元素组成】C 59.56% H 4.61% Br 30.48% N 5.34%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(R)-(I)

The condensation of (S)-1-(4-bromophenyl)-1-phenylmethylamine (S)-(I) with phenylboronic acid (II) by means of Pd(OAc)2, PPh3 and Na2CO3 in propanol/water gives the corresponding biphenyl derivative (S)-(III), which is condensed with 3-bromopropanal dimethylacetal (IV) by means of K2CO3 in DMF yielding the secondary amine (S)-(V). The reaction of (S)-(V) with refluxing butyl formate (VI) affords the formamide (S)-(VII), which is cyclized with ammonium acetate in acetic acid to furnish the (S)-enantiomer of the target compound. The corresponding (R)-enantiomer has been obtained by the same reaction sequence but starting from (R)-1-(4-bromophenyl)-1-phenylmethylamine (R)-(I).

参考文献中间体

合成目标

【1】 Botta, M.; et al.; Chiral azole derivatives.4.Enantiomers of bifonazole and related antifungal agents. Synthesis, configuration assignment, and biological evaluation. J Org Chem 2000, 65, 15, 4736.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(S)-(I)	38286	(S)-(4-bromophenyl)(phenyl)methanamine; (S)-(4-bromophenyl)(phenyl)methylamine		C₁₃H₁₂BrN	详情	详情
(S)-(III)	38287	(S)-[1,1'-biphenyl]-4-yl(phenyl)methylamine; (S)-[1,1'-biphenyl]-4-yl(phenyl)methanamine		C₁₉H₁₇N	详情	详情
(S)-(V)	38288	N-[(S)-[1,1'-biphenyl]-4-yl(phenyl)methyl]-2,2-dimethoxy-1-ethanamine; N-[(S)-[1,1'-biphenyl]-4-yl(phenyl)methyl]-N-(2,2-dimethoxyethyl)amine		C₂₃H₂₅NO₂	详情	详情
(S)-(VII)	38290	(S)-[1,1'-biphenyl]-4-yl(phenyl)methyl(2,2-dimethoxyethyl)formamide; 4-[(S)-[(2,2-dimethoxyethyl)(formyl)amino](phenyl)methyl]-1,1'-biphenyl		C₂₄H₂₅NO₃	详情	详情
(R)-(I)	38291	(R)-(4-bromophenyl)(phenyl)methanamine; (R)-(4-bromophenyl)(phenyl)methylamine		C₁₃H₁₂BrN	详情	详情
(R)-(III)	38292	(R)-[1,1'-biphenyl]-4-yl(phenyl)methanamine; (R)-[1,1'-biphenyl]-4-yl(phenyl)methylamine		C₁₉H₁₇N	详情	详情
(R)-(V)	38293	N-[(R)-[1,1'-biphenyl]-4-yl(phenyl)methyl]-N-(2,2-dimethoxyethyl)amine; N-[(R)-[1,1'-biphenyl]-4-yl(phenyl)methyl]-2,2-dimethoxy-1-ethanamine		C₂₃H₂₅NO₂	详情	详情
(R)-(VII)	38294	4-[(R)-[(2,2-dimethoxyethyl)(formyl)amino](phenyl)methyl]-1,1'-biphenyl; (R)-[1,1'-biphenyl]-4-yl(phenyl)methyl(2,2-dimethoxyethyl)formamide		C₂₄H₂₅NO₃	详情	详情
(II)	16593	Phenylboronic acid；Benzeneboronic acid;Phenylboron dihydroxide	98-80-6	C₆H₇BO₂	详情	详情
(IV)	29689	3-bromo-1,1-dimethoxypropane; 3-bromo-1-methoxypropyl methyl ether	36255-44-4	C₅H₁₁BrO₂	详情	详情
(VI)	38289	butyl formate	592-84-7	C₅H₁₀O₂	详情	详情

Extended Information