Cyclopropyl ring opening by alpha alkylation of an aldehyde with a polycyclic olefin
AssigneeFirmenich SA
InventorJulie Quintaine
Life of this patent
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Abstract
Described herein is a process including alpha alkylation of an aldehyde with a polycyclic olefin followed by a ring opening step in order to provide a compound of formula in a form of any one of its stereoisomers or a mixture thereof and where n represents 1 to 4 and R2 to R5 represent independently of each other, a hydrogen atom or a C1-6 linear alkyl group or a C3-6 branched alkyl group; and R3 and R4 or R5 or, alternatively, R2 and R3 when taken together form a saturated or unsaturated optionally substituted 5 or 6 membered carbocyclic ring.
Claims18
A process for the preparation of a compound of formula
- in a form of any one of its stereoisomers or a mixture thereof and wherein
- n represents 1 to 4,
- R1 represents a hydrogen or a C1-8 linear alkyl group;
- R2 to R5 represent independently of each other, a hydrogen atom or a C1-6 linear alkyl group or a C3-6 branched alkyl group;
- and
- R3 and R4 or R5 or, alternatively, R2 and R3 when taken together form a saturated or unsaturated optionally substituted 5 or 6 membered carbocyclic ring;
- comprising the step of an alpha alkylation of an aldehyde of formula R1—CH2—CHO wherein R1 has the same meaning as described above with an olefin compound being a fused or bridged bicyclic or tricyclic compound with a methylene group in alpha position of a cyclopropyl ring junction;
- said step being performed in the presence of a photoredox catalyst, a hydrogen atom transfer donor, a secondary amine and light.
A compound of formula
- in a form of any one of its stereoisomers or a mixture thereof and wherein n represents 1 to 4;
- R1 represents a hydrogen or a C1-8 linear alkyl group and R2 to R5 represent independently of each other, a hydrogen atom or a C1-6 linear alkyl group or a C3-6 branched alkyl group;
- and R3 and R4 or R5 or, alternatively, R2 and R3 when taken together form a saturated or unsaturated optionally substituted 5 or 6 membered carbocyclic ring.
The perfumed consumer product according to claim 16, wherein the product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product, or a home care product.
The perfumed consumer product according to claim 17, wherein the perfumed consumer product is a fine perfume, a splash or eau de perfume, a cologne, an shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtaincare product, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard-surface detergent, a leather care product, or a car care product.
Dependencies are inferred from the claim text.