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    PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE
    1.
    发明申请
    PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE 审中-公开

    公开(公告)号：US20200048275A1

    公开(公告)日：2020-02-13

    申请号：US16485563

    申请日：2018-02-05

    申请人： BASF Agro B.V.

    发明人： Stefan BENSON ,  Michael RACK ,  Roland GOETZ ,  Bernd WOLF ,  Joachim GEBHARDT ,  Helmut KRAUS

    IPC分类号： C07D493/08

    摘要： This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso-propyl-7-oxabicyclo[2.2.1]heptane of the formula (I), (I) any one of its individual enantiomers or any non-racemic mixture thereof comprising the steps of (a) deprotonating (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), (II) any one of its individual enantiomers or any non-racemic mixture thereof in the presence of at least one base of the formula [Mm+]n [An-]m (III) wherein Mm+ represents a m-valent metal cation wherein m is an integer of 1 or 2, and An_ represents a n-valent anion wherein n is an integer of 1 or 2, said base being capable of forming a solvent S1 selected from water, a C1-C4 alkyl alcohol or any combination thereof under the reaction conditions, to form a metal alkoxide or metal alkoxide solvate of the formula (IV), (IV) any one of its individual enantiomers or any non-racemic mixture thereof wherein Mm+, m and the solvent S1 have the same meaning as defined for the base of formula (III), and x denotes a number from 0 to 10, and (b) reacting the metal alkoxide or metal alkoxide solvate of the formula (IV), any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (V), (V) wherein X is a leaving group, wherein the steps (a) and (b) are conducted in the presence of at least one inert organic solvent S2 and comprise a further step of (c) simultaneously removing the solvent S1 from the reaction mixture.

    Process for Preparing 2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane
    2.
    发明申请
    Process for Preparing 2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane 审中-公开

    公开(公告)号：US20200031792A1

    公开(公告)日：2020-01-30

    申请号：US16334152

    申请日：2017-09-07

    申请人： BASF Agro B.V.

    发明人： Stefan BENSON ,  Michael RACK ,  Bernd WOLF ,  Roland GOETZ ,  Joachim GEBHARDT ,  Helmut KRAUS

    IPC分类号： C07D307/00

    摘要： This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group in the presence of at least one base capable of forming water or a C1-C4 alkyl alcohol under the reaction conditions, and at least one inert organic solvent, and (b) simultaneously removing water, the C1-C4 alkyl alcohol or any mixture thereof from the reaction mixture.

    Method for Separating Optically Active Hydroxy Cineole Derivatives
    3.
    发明申请
    Method for Separating Optically Active Hydroxy Cineole Derivatives 审中-公开

    公开(公告)号：US20200148697A1

    公开(公告)日：2020-05-14

    申请号：US16614400

    申请日：2018-05-09

    申请人： BASF Agro B.V.

    发明人： Klaus DITRICH ,  Michael RACK ,  Stefan BENSON ,  Roland GOETZ ,  Helmut KRAUS

    IPC分类号： C07D493/08 ,  C07B57/00

    摘要： The present invention relates to a method for separating an optically active hydroxy cineole derivatives by lixiviation and crystallization and enantiomerically pure optically active hydroxy cineole derivatives of purity greater than 99.5% that have been prepared by this process. The present invention further relates to use of the desired enantiomer having enantiomeric excess of at least 99.5% ee as prepared according to the present invention, for the synthesis of enantiomerically pure 7-oxabicyclo[2.2.1]heptane derivatives.