A practical synthesis of para di- and mono-substituted benzhydrylamines from benzhydrol precursors

被引:0
|
作者
Laurent, M [1 ]
Marchand-Brynaert, J [1 ]
机构
[1] Univ Catholique Louvain, Lab Chim Organ Synthese, B-1348 Louvain, Belgium
来源
SYNTHESIS-STUTTGART | 2000年 / 05期
关键词
benzhydrylamines; chiral chromatography; (+)-4-chlorobenzhydrylamine; (-)-4-chlorobenzhydrylamine; hydrolyses; deprotection;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of para-substituted benzhydrylamines 6 were obtained by substitution of the corresponding benzhydrol precursors 1 with phenyl carbamate 2 under acidic conditions, followed by basic hydrolysis of the carbamate intermediates 3. One unsymmetrical intermediate 3i has been resolved by preparative chiral chromatography. Subsequent deprotection of the carbamate function led to the recovery of enantiomerically pure (+)- and (-)-4-chlorobenzhydryl amines.
引用
收藏
页码:667 / 672
页数:6
相关论文
共 50 条
  • [21] STUDIES IN SULPHANILAMIDES .8. PARA-ACETSULPHANILAMIDE DERIVATIVES SUBSTITUTED IN N1-POSITION BY MONO-SUBSTITUTED AND DI-SUBSTITUTED THIURETS
    SWAMINATHAN, S
    GUHA, PC
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1946, 23 (09) : 319 - 323
  • [22] An Efficient Synthesis of Mono-Substituted Benzyl Ferrocene Derivatives
    Abdullah, Razack
    Chung, Keunwoo
    Kim, Young-Wun
    Hong, In Seok
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01) : 32 - 35
  • [23] Effect of substituents on the energies of exited states of mono-substituted and di-substituted benzenes
    Frolov, AN
    Minaev, BF
    ZHURNAL ORGANICHESKOI KHIMII, 1998, 34 (12): : 1828 - 1834
  • [24] Synthesis of mono-substituted derivatives of 6-aminoquinoline
    Tian Lan~(a
    ChineseChemicalLetters, 2011, 22 (03) : 253 - 255
  • [25] Selective synthesis of chlorohydrogermanes from mono-, di-, and trihydrogermanes
    Ohshita, J
    Toyoshima, Y
    Iwata, A
    Tang, HQ
    Kunai, A
    CHEMISTRY LETTERS, 2001, (09) : 886 - 887
  • [26] SYNTHESIS OF NOVEL MONO-SUBSTITUTED AND DIARYL-SUBSTITUTED [2.2]PARACYCLOPHANES
    ROZENBERG, VI
    SERGEEVA, EV
    KHARITONOV, VG
    VORONTSOVA, NV
    VORONTSOV, EV
    MIKULSHINA, VV
    RUSSIAN CHEMICAL BULLETIN, 1994, 43 (06) : 1018 - 1023
  • [27] An efficient synthesis of mono-, di-, and tri-substituted 1,3-thiazoles employing functionalized thioamides as thiocarbonyl precursors
    Sheela, Kalleshappa
    Santhosh, Chikkappaiahnayaka
    Singh, Krishna Ravi
    Sharath, Kalleshappa
    Sadashiva, Maralinganadoddi P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (17) : 3490 - 3501
  • [28] C-13 NMR-SPECTRA OF MONO-SUBSTITUTED AND DI-SUBSTITUTED FLUORENES
    ZAKHAROV, VF
    ZVOLINSKII, VP
    PROSTAKOV, NS
    ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (08): : 1697 - 1703
  • [29] SYNTHESIS AND CHARACTERIZATION OF A SERIES OF MONO-SUBSTITUTED AMIDO-TETRAPHENYLPORPHYRINS
    ZHANG, H
    SIMONIS, U
    WALKER, FA
    KIPP, C
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 185 - INOR
  • [30] A CONVENIENT SYNTHESIS OF 4(5)-MONO-SUBSTITUTED, 4,5-DI-SUBSTITUTED, AND 2,4,5-TRI-SUBSTITUTED IMIDAZOLES
    IDDON, B
    KHAN, N
    TETRAHEDRON LETTERS, 1986, 27 (14) : 1635 - 1638