JPH047349B2 - - Google Patents
Info
- Publication number
- JPH047349B2 JPH047349B2 JP59061224A JP6122484A JPH047349B2 JP H047349 B2 JPH047349 B2 JP H047349B2 JP 59061224 A JP59061224 A JP 59061224A JP 6122484 A JP6122484 A JP 6122484A JP H047349 B2 JPH047349 B2 JP H047349B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolitidine
- compound
- formula
- group
- hydrogen
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 23
- -1 p-toluenesulfonyloxy group Chemical group 0.000 claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000006243 carbonyl protecting group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 230000001766 physiological effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229940075930 picrate Drugs 0.000 description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- CKAKSKNWORUGDA-UHFFFAOYSA-N ethyl 6-chlorohex-2-enoate Chemical compound CCOC(=O)C=CCCCCl CKAKSKNWORUGDA-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 1
- DOQLCJMCQWQQHK-UHFFFAOYSA-N 4-chlorobutanal Chemical compound ClCCCC=O DOQLCJMCQWQQHK-UHFFFAOYSA-N 0.000 description 1
- 206010027646 Miosis Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- WJCXADMLESSGRI-UHFFFAOYSA-N phenyl selenohypochlorite Chemical compound Cl[Se]C1=CC=CC=C1 WJCXADMLESSGRI-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59061224A JPS60204787A (ja) | 1984-03-30 | 1984-03-30 | ピロリチジン化合物の製法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59061224A JPS60204787A (ja) | 1984-03-30 | 1984-03-30 | ピロリチジン化合物の製法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60204787A JPS60204787A (ja) | 1985-10-16 |
JPH047349B2 true JPH047349B2 (fr) | 1992-02-10 |
Family
ID=13165020
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59061224A Granted JPS60204787A (ja) | 1984-03-30 | 1984-03-30 | ピロリチジン化合物の製法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60204787A (fr) |
-
1984
- 1984-03-30 JP JP59061224A patent/JPS60204787A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS60204787A (ja) | 1985-10-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH1192423A (ja) | トリフルオロ酢酸及びクロロジフルオロ酢酸のメチルエステル又はエチルエステルの製造方法 | |
RU2404169C2 (ru) | Способ получения делмопинола и его производных | |
Dowd et al. | Synthesis of 1, 5-disubstituted tricyclo [2.1. 0.02, 5] pentanes. The crystal and molecular structures of 1, 5-bis (acetoxymethyl) tricyclo [2.1. 0.02, 5] pentan-3-one | |
DE69812079T2 (de) | Verfahren zur herstellung eines buthylthuio-isochinolinderivates und zwischenprodukte dafür | |
JPH047349B2 (fr) | ||
L'abbé et al. | Approaches towards the synthesis of allenyl azides | |
JP2023548919A (ja) | ジピロメテン-1-オン系化合物及びその製造方法 | |
CN112592306A (zh) | 吡咯啉酮类化合物及其合成方法 | |
EP0025569B1 (fr) | Amides contenant du silicium, leur préparation, intermédiaires dans leur préparation et compositions pharmaceutiques les contenant | |
CN114805168B (zh) | 吡咯啉酮类化合物及其合成方法 | |
DE19853558A1 (de) | Verfahren zur Herstellung von 2,3-Dihydroindolen (Indolinen), neuartige 2,3-Dihydroindole sowie deren Verwendung | |
WO2002022619A1 (fr) | Procede de preparation de derives d'acide 7-oxabicyclo[2,2,1]hept-5-ene-2-carboxylique | |
KR940006531B1 (ko) | 피리딘 유도체의 제조방법 | |
CN114380863A (zh) | 金鸡纳碱衍生的nnp配体及其制备方法与用途 | |
JP4064645B2 (ja) | 多置換シクロアルケン類の新規製造法 | |
US6313353B1 (en) | Method for producing an optically active acyloin | |
CN114105862A (zh) | 盐酸多奈哌齐杂质及其制备方法 | |
JPH05194459A (ja) | 光学活性なレボブノロール合成中間体およびその製造方法 | |
JPH0597735A (ja) | 光学活性二級アルコ−ルの製造方法 | |
JPH0376313B2 (fr) | ||
JPS6219542A (ja) | 光学活性アルコ−ル類の製造方法 | |
JPH07233164A (ja) | ピロカルピン誘導体の製造方法 | |
JPS61155352A (ja) | 4−クロロ−3−アルケン酸およびその製造方法 | |
JPS60252430A (ja) | アセチレン化合物類の製法 | |
JPH03112963A (ja) | 光学活性3,4―デヒドロピロリジン化合物の製造方法 |