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US 9,994,508 B2Granted
Versatile and functionalised intermediates for the synthesis of vitamin D and novel vitamin D derivatives
AssigneeEndotherm GmbH
InventorsBorja Lopez Perez, Rita Sigueiro Ponte, Miguel A. Maestro Saavedra, Antonio Mourino Mosquera
Life of this patent
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Abstract
Novel intermediates for the complete synthesis of vitamin D are provided that allow a great versatility of functional groups in the final vitamin derivatives. Vitamin derivatives that are epimeric in position 3 and vitamin derivatives with a wide range of functionalities in position 18, including compounds with isotopic labelling are provided.
Claims3
A process for preparing compounds of formula (XIV), comprising:
- a) reacting a compound of formula (XV) with a base and an isocyanate comprising phenyl, t-butyl, p-methylphenyl, or o-methylphenyl isocyanate to form a mixture comprising a carbamate,
- wherein R7 is —SiP1P2P3, each of P1, P2, P3 is independently selected from the group consisting of alkyl, aryl, arylalkyl and heterocycle,
- b) adding a copper salt and X—Li to the mixture of step a), wherein X is selected from the group consisting of hydrogen, (C1-C6) alkyl, aryl, arylalkyl, heteroalkyl and heterocycle, and
- c) obtaining compounds of formula (XIV):
1 more element
A process for preparing compounds of formula (XIV), comprising:
- 1) preparing compounds of formula (XVI)
- by:
- protecting the hydroxyl group of oct-1-en-7-yn-3-ol;
- treating the resulting compound with a base and adding a silylating agent;
- and
- performing a Pauson-Khand reaction with the resultant compound of said treating using a CO donor metal complex and a cooxidant;
- 2) reacting a compound of formula (XVI) with a reducing agent to prepare compounds of formula (XV)
- wherein R7 is —SiP1P2P3, each of P1, P2, P3 is independently selected from the group consisting of alkyl, aryl, arylalkyl and heterocycle
- 3) reacting a compound of formula (XV) with a base and an isocyanate comprising phenyl, t-butyl, p-methylphenyl, or o-methylphenyl isocyanate to form a mixture comprising a carbamate, and adding a copper salt and X—Li to the mixture to prepare compounds of formula (XIV), wherein X is selected from the group consisting of hydrogen, (C1-C6) alkyl, aryl, arylalkyl, heteroalkyl and heterocycle;
- and
- c) obtaining compounds of formula (XIV):
8 more elements
Dependencies are inferred from the claim text.