Method of preparing substituted bicyclo[1.1.1] pentanes
AssigneeSpirochem AG
InventorsYoshikazu Suzuki, Daniel Jimenez-Teja, Christophe Salomé, Thomas Fessard
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Abstract
A process for the preparation of a class of molecules, namely bicyclo[1.1.1]pentanes and derivatives thereof by reaction of [1.1.1]propellane with a variety of reagents under irradiation and/or in the presence of radical initiators to obtain bicyclo[1.1.1]pentanes asymmetrically substituted at position 1 and 3, which are useful as intermediates for the preparation of asymmetrically 1,3-disubstituted bicyclo[1.1.1]pentane derivatives and various physiologically active substances or materials containing these structures.
Claims19
A one-step process for producing an asymmetrically substituted compound of formula I,
- comprising the step of reacting [1.1.1]propellane of formula II
- with a compound of formula III, wherein
- Z is C, S or S(═O);
- Y is R1—C(═O)—, R1OC(═O)—, —CH2F, —CHF2, —CF3, —C2F5, —C3F7, —CN, R1R2NC(═O)—, R1SC(═O)—, R1R2N—, —NO2, or —CH(═NOR1), wherein R1 and R2 are independently of each other H, saturated linear or branched —(C1-C20)alkyl, or aryl or R1 and R2 form together a cycle;
- and
- X is halogen, —OR1, or —NR1R2, wherein R1 and R2 are independently of each other H, saturated linear or branched —(C1-C20)alkyl, or aryl or R1 and R2 form together a cycle.
Dependencies are inferred from the claim text.