AR039099A1 - PROCEDURE TO PREPARE 7ALFA-METHYLESTEROIDS - Google Patents

PROCEDURE TO PREPARE 7ALFA-METHYLESTEROIDS

Info

Publication number
AR039099A1
AR039099A1 ARP030100996A AR039099A1 AR 039099 A1 AR039099 A1 AR 039099A1 AR P030100996 A ARP030100996 A AR P030100996A AR 039099 A1 AR039099 A1 AR 039099A1
Authority
AR
Argentina
Prior art keywords
methyl
atom
general formula
ch3mgx
hydroxy
Prior art date
Application number
Other languages
Spanish (es)
Inventor
Setphan Vettel
Agnes Matzeit
Orlin Petrov
Evelin Amoulong-Kirstein
Marc Willuhn
Original Assignee
Schering Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Ag filed Critical Schering Ag
Publication of AR039099A1 publication Critical patent/AR039099A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
    • C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Un procedimiento para preparar 7a-metilesteroides de la fórmula general (1) partiendo de compuestos de la fórmula general (2) que se transforman en un solvente aprótico en presencia de 1-30% en moles de un compuesto de cobre CuYnLm con 1-3 equivalentes molares de CH3MgX, y a continuación con un ácido fuerte. El procedimiento se caracteriza porque se obtienen 7a-metilesteroides con buenos rendimientos, elevada pureza química y elevadas purezas diastereoméricas. El procedimiento se caracteriza porque se produce menor cantidad de residuos con un mayor rendimiento. Por ello, el procedimiento es apropiado para preparar 7a-metilesteroides en gran escala. Reivindicación 1: Procedimiento caracterizado porque es para preparar 7a-metilesteroides de la fórmula general (1) donde R10 es H o metilo; R11a es H, R11b es H, hidroxi, F u -OC(O)R19, o junto con R11a es un átomo de O; R19 es un grupo alquilo C1-12; R13 es H, metilo o etilo; R17a es H; R17b es H, hidroxi, R19, -OR19, -OC(O)R19, o junto con R17a es un átomo de O, o R17b también puede ser el grupo -OM', donde M' es SiR1R2R3; R1, R2, R3 son, independientemente entre si, R19, -OR19, bencilo, arilo, Oarilo, que comprende los siguientes pasos: a) convertir un compuesto de la fórmula general (2) donde R10 es H o metilo; R11a es H; R11b es H, F, u -OC(O)R19, o junto con R11a es un átomo de O; R19 es un grupo alquilo C1-12, R13 es H, metilo o etilo, R17a es H, R17b es H, hidroxi, R19, -OR19, -OC(O)R19, o junto con R17a es un átomo de O, o R17b también puede ser el grupo -OM, donde M es -QR1R2R3 o -QR1R2, Q es boro, aluminio, silicio; R1, R2 y R3 son independientemente entre sí, R19, -OR19, bencilo, arilo, Oarilo, en un solvente aprótico con 1-3 equivalentes molares de CH3MgX, cuando X es Cl, Br, o yodo, o con 0,5-3 equivalentes molares de CH3MgX, cuando X es metilo, en presencia de 1 a 30 % en moles de un compuesto de cobre CuYnLm, donde Y es un anión inorgánico u orgánico, L es un ligando, n es 1 o 2; m es 0 o un número entero natural; b) agregar un ácido mineral fuerte a la mezcla de reacción y posterior agitación, c) aislar y purificar.A process for preparing 7a-methyl steroids of the general formula (1) starting from compounds of the general formula (2) which are transformed into an aprotic solvent in the presence of 1-30 mol% of a CuYnLm copper compound with 1-3 molar equivalents of CH3MgX, and then with a strong acid. The process is characterized in that 7a-methyl steroids are obtained with good yields, high chemical purity and high diastereomeric purities. The procedure is characterized in that less waste is produced with a higher yield. Therefore, the procedure is appropriate for preparing large-scale 7a-methylstyles. Claim 1: Method characterized in that it is for preparing 7a-methyl steroids of the general formula (1) wherein R 10 is H or methyl; R11a is H, R11b is H, hydroxy, F or -OC (O) R19, or together with R11a is an O atom; R19 is a C1-12 alkyl group; R13 is H, methyl or ethyl; R17a is H; R17b is H, hydroxy, R19, -OR19, -OC (O) R19, or together with R17a is an atom of O, or R17b can also be the group -OM ', where M' is SiR1R2R3; R1, R2, R3 are, independently of each other, R19, -OR19, benzyl, aryl, Oaryl, comprising the following steps: a) converting a compound of the general formula (2) where R10 is H or methyl; R11a is H; R11b is H, F, or -OC (O) R19, or together with R11a is an O atom; R19 is a C1-12 alkyl group, R13 is H, methyl or ethyl, R17a is H, R17b is H, hydroxy, R19, -OR19, -OC (O) R19, or together with R17a is an atom of O, or R17b can also be the group -OM, where M is -QR1R2R3 or -QR1R2, Q is boron, aluminum, silicon; R1, R2 and R3 are independently from each other, R19, -OR19, benzyl, aryl, Oaryl, in an aprotic solvent with 1-3 molar equivalents of CH3MgX, when X is Cl, Br, or iodine, or with 0.5- 3 molar equivalents of CH3MgX, when X is methyl, in the presence of 1 to 30 mol% of a CuYnLm copper compound, where Y is an inorganic or organic anion, L is a ligand, n is 1 or 2; m is 0 or a natural integer; b) add a strong mineral acid to the reaction mixture and subsequent stirring, c) isolate and purify.

ARP030100996 2002-03-21 2003-03-21 PROCEDURE TO PREPARE 7ALFA-METHYLESTEROIDS AR039099A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2002113371 DE10213371C1 (en) 2002-03-21 2002-03-21 Process for the preparation of 7alpha methyl steroids

Publications (1)

Publication Number Publication Date
AR039099A1 true AR039099A1 (en) 2005-02-09

Family

ID=28050836

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP030100996 AR039099A1 (en) 2002-03-21 2003-03-21 PROCEDURE TO PREPARE 7ALFA-METHYLESTEROIDS

Country Status (5)

Country Link
AR (1) AR039099A1 (en)
AU (1) AU2003212373A1 (en)
DE (1) DE10213371C1 (en)
TW (1) TW200400825A (en)
WO (1) WO2003079961A2 (en)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3341557A (en) * 1961-06-05 1967-09-12 Upjohn Co 7-methyltestosterones
US3470216A (en) * 1966-11-29 1969-09-30 Du Pont Selected 17,17-difluoro unsaturated androstanes
FR2054527B1 (en) * 1969-07-28 1973-06-08 Roussel Uclaf
US4000273A (en) * 1973-11-01 1976-12-28 Richardson-Merrell Inc. Method for the control of fertility
DE2558088C2 (en) * 1975-12-19 1985-05-30 Schering AG, 1000 Berlin und 4709 Bergkamen Process for the preparation of 4-androstene-3,17-dione derivatives
SK882003A3 (en) * 2000-07-28 2003-07-01 Akzo Nobel Nv 16alpha-substituted steroid compounds, pharmaceutical composition comprising same and their use
ES2336439T3 (en) * 2002-01-21 2010-04-13 N.V. Organon PROCESS FOR THE PREPARATION OF 7-ALFA-METHYLESTEROIDS.

Also Published As

Publication number Publication date
WO2003079961A3 (en) 2004-03-11
DE10213371C1 (en) 2003-12-24
TW200400825A (en) 2004-01-16
AU2003212373A1 (en) 2003-10-08
AU2003212373A8 (en) 2003-10-08
WO2003079961A2 (en) 2003-10-02

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Legal Events

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FA Abandonment or withdrawal