GB1240698A - Methylenation process and reagent - Google Patents
Methylenation process and reagentInfo
- Publication number
- GB1240698A GB1240698A GB4908168A GB4908168A GB1240698A GB 1240698 A GB1240698 A GB 1240698A GB 4908168 A GB4908168 A GB 4908168A GB 4908168 A GB4908168 A GB 4908168A GB 1240698 A GB1240698 A GB 1240698A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylene
- reagent
- yield
- weight
- hydroxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000003153 chemical reaction reagent Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 238000005822 methylenation reaction Methods 0.000 title 1
- -1 methylene steroids Chemical class 0.000 abstract 4
- QKEHMKYPLXJXOU-XSEPRYCASA-N (5R,8S,9S,10R,13S,14S)-10,13-dimethyl-6-methylidene-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C=C1C[C@@H]2[C@H](CC[C@@]3(CCC[C@H]32)C)[C@]3(CCCC[C@H]13)C QKEHMKYPLXJXOU-XSEPRYCASA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- GZSCFURMBHMSCE-JKNDIDBPSA-N (6s,8r,9s,10r,13s,14s)-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@H]21 GZSCFURMBHMSCE-JKNDIDBPSA-N 0.000 abstract 1
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 abstract 1
- QARLZVKJBNMVTR-UHFFFAOYSA-M C=C1OCCC1.I[Zn] Chemical compound C=C1OCCC1.I[Zn] QARLZVKJBNMVTR-UHFFFAOYSA-M 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 230000001195 anabolic effect Effects 0.000 abstract 1
- 230000001548 androgenic effect Effects 0.000 abstract 1
- 150000001441 androstanes Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000005646 oximino group Chemical group 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 230000003637 steroidlike Effects 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- A—HUMAN NECESSITIES
- A47—FURNITURE; DOMESTIC ARTICLES OR APPLIANCES; COFFEE MILLS; SPICE MILLS; SUCTION CLEANERS IN GENERAL
- A47L—DOMESTIC WASHING OR CLEANING; SUCTION CLEANERS IN GENERAL
- A47L17/00—Apparatus or implements used in manual washing or cleaning of crockery, table-ware, cooking-ware or the like
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
1,240,698. Halo-zinc-methylene reagent; preparation of methylene steroids. G. D. SEARLE & CO. 16 Oct., 1968 [17 Oct., 1967], No. 49081/68. Headings C2J and C2U. A process for the manufacture of a halozinc methylene reagent comprises contacting a zinclead couple with a methylene halide in tetrahydrofuran or an alkylene glycol ether or dialkoxy ether at elevated temperature. Preferably CH 2 Br 2 or CH 2 I 2 and T.H.F. are used. A typical iodozinc methylene tetrahydrofuran reagent crystallized from solution contains 15-25% by weight Zn, 50-65% by weight I and 13-20% by weight C. The reagent may be used to react with a reactive steroidal ketone to produce a methylene steroid. Steroid derivatives which may be used include those of the pregnane, estrane and androstane series. The ketone may be activated by an adjacent hydroxy, acyloxy or oximino function. The ketone group may be in the 3-, 20- or 6-positions. It is stated that 6-methyleneandrostane - 3(#,5α,17# - triol, which may be made from the corresponding 3,17-diacetate formed by this method, may be reacted with CrO 3 to yield the 3,17-dione, hydrogenated using a platinum catalyst to yield the 6α-methyl derivative, and dehydrated with SOCl 2 to yield 6α - methyl androst - 4 - ene - 3,17 - dione, which may then be reduced with NaBH 4 to yield 17#- hydroxy - 6α - methyl androst - 4 - en - 3 - one, a compound having both anabolic and androgenic properties. A number of other methylenesteroid products are also described, and the conversion of 3# - benzyloxy - 5α - hydroxy-6- methylenepregnan - 20 - one 20 - ethylene ketal to the free 20-one, the formation of 6-methylenandrostane - 3#,5α,l7# - triol triacetate from the 3,17-diacetate and the formation of the corresponding tripropionate from the dipropionate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US865965A US3634469A (en) | 1968-10-16 | 1969-10-13 | Methylenated steroids and process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67578867A | 1967-10-17 | 1967-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1240698A true GB1240698A (en) | 1971-07-28 |
Family
ID=24711977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4908168A Expired GB1240698A (en) | 1967-10-17 | 1968-10-16 | Methylenation process and reagent |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1803276A1 (en) |
| FR (1) | FR1588400A (en) |
| GB (1) | GB1240698A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE7137606U (en) | 1972-12-21 | Roeder W | Device for cleaning a collecting rake arranged at the bottom of the inlet to a wastewater treatment plant with a straight rake rear side |
-
1968
- 1968-10-16 GB GB4908168A patent/GB1240698A/en not_active Expired
- 1968-10-16 FR FR1588400D patent/FR1588400A/fr not_active Expired
- 1968-10-16 DE DE19681803276 patent/DE1803276A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1803276A1 (en) | 1969-06-04 |
| FR1588400A (en) | 1970-04-10 |
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