JPH041750B2 - - Google Patents
Info
- Publication number
- JPH041750B2 JPH041750B2 JP58141882A JP14188283A JPH041750B2 JP H041750 B2 JPH041750 B2 JP H041750B2 JP 58141882 A JP58141882 A JP 58141882A JP 14188283 A JP14188283 A JP 14188283A JP H041750 B2 JPH041750 B2 JP H041750B2
- Authority
- JP
- Japan
- Prior art keywords
- lithium
- chlorocarbonate
- formula
- lower alkyl
- hour
- 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
- -1 alkyl chlorocarbonate Chemical compound 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XRPLBLPRUDFFCC-UHFFFAOYSA-N methyl 18-oxo-3,11,12,14,15,16,17,19,20,21-decahydro-1h-yohimban-19-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C1CC3C(C(=O)OC)C(=O)CCC3CN1CC2 XRPLBLPRUDFFCC-UHFFFAOYSA-N 0.000 description 5
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 4
- 229960000317 yohimbine Drugs 0.000 description 4
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 238000006257 total synthesis reaction Methods 0.000 description 3
- CWOYLIJQLSNRRN-UHFFFAOYSA-N Harmalan Chemical compound N1C2=CC=CC=C2C2=C1C(C)=NCC2 CWOYLIJQLSNRRN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- LEXXFFUKMREIKL-LXIYXOSZSA-N (1s,15r,20r)-3,11,12,14,15,16,17,19,20,21-decahydro-1h-yohimban-18-one Chemical group C1=CC=C2C(CCN3C[C@@H]4CCC(C[C@H]4C[C@H]33)=O)=C3NC2=C1 LEXXFFUKMREIKL-LXIYXOSZSA-N 0.000 description 1
- NSBVOLBUJPCPFH-UHFFFAOYSA-N 5h-pyrido[3,2-b]indole Chemical compound C1=CN=C2C3=CC=CC=C3NC2=C1 NSBVOLBUJPCPFH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- RHIUIXSTQSQFAX-UHFFFAOYSA-N lithium ethyl(methyl)azanide Chemical compound [Li+].CC[N-]C RHIUIXSTQSQFAX-UHFFFAOYSA-N 0.000 description 1
- NVMMPHVQFFIBOS-UHFFFAOYSA-N lithium;dibutylazanide Chemical compound [Li+].CCCC[N-]CCCC NVMMPHVQFFIBOS-UHFFFAOYSA-N 0.000 description 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
- YDGSUPBDGKOGQT-UHFFFAOYSA-N lithium;dimethylazanide Chemical compound [Li+].C[N-]C YDGSUPBDGKOGQT-UHFFFAOYSA-N 0.000 description 1
- OWYFNXMEEFAXTO-UHFFFAOYSA-N lithium;dipropylazanide Chemical compound [Li+].CCC[N-]CCC OWYFNXMEEFAXTO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BLGXFZZNTVWLAY-DIRVCLHFSA-N rauwolscine Chemical compound C1=CC=C2C(CCN3C[C@H]4CC[C@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-DIRVCLHFSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- JUPDIHMJFPDGMY-DEYYWGMASA-N yohimban Chemical group C1=CC=C2C(CCN3C[C@@H]4CCCC[C@H]4C[C@H]33)=C3NC2=C1 JUPDIHMJFPDGMY-DEYYWGMASA-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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58141882A JPS6032787A (ja) | 1983-08-04 | 1983-08-04 | ヨヒンビノン類の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58141882A JPS6032787A (ja) | 1983-08-04 | 1983-08-04 | ヨヒンビノン類の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6032787A JPS6032787A (ja) | 1985-02-19 |
| JPH041750B2 true JPH041750B2 (en]) | 1992-01-14 |
Family
ID=15302352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58141882A Granted JPS6032787A (ja) | 1983-08-04 | 1983-08-04 | ヨヒンビノン類の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6032787A (en]) |
-
1983
- 1983-08-04 JP JP58141882A patent/JPS6032787A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6032787A (ja) | 1985-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111620869B (zh) | 叔丁基-1,7-二氮杂螺[3.5]壬烷-1-甲酸基酯的合成方法 | |
| EP0441160B1 (en) | Process for preparing levo and dextro fenfluramine | |
| JPH0776209B2 (ja) | 光学活性３―ヒドロキシピロリジン誘導体の製造方法 | |
| CN118598812A (zh) | 石杉碱甲关键中间体的合成方法 | |
| JPH0246590B2 (en]) | ||
| CN113773229B (zh) | α,β-不饱和氨基酸衍生物及其DL-硒-甲基硒代氨基酸衍生物、合成方法和应用 | |
| JPH041750B2 (en]) | ||
| JPH0551345A (ja) | 光学活性３−置換−２−ノルボルナノンの製造法 | |
| CN109678738B (zh) | 一种合成(2s,3s)-3-氨基-二环[2.2.2]辛烷-2-甲酸酯的方法 | |
| CN108409615B (zh) | 一种合成对映纯叔丁基亚磺酰胺的方法 | |
| JPS62201842A (ja) | ３−ヒドロキシシクロペント−４−エン−１−オン類の製造法 | |
| JP3547590B2 (ja) | 不斉ジルコニウム触媒 | |
| CN119285532B (zh) | 一种N-Boc保护L-beta-高哌啶酸甲酯的合成方法 | |
| JP4057088B2 (ja) | ピロリジン誘導体の製造方法 | |
| JP2015137279A (ja) | シクロヘキサン−１，４−ジカルボン酸ビス［４−（６−アクリロイルオキシヘキシル）フェニル］の製造方法 | |
| JPH0429673B2 (en]) | ||
| KR101087500B1 (ko) | 바이나프톨 알데히드 유도체 및 그의 중간체의 제조방법 | |
| JP2680683B2 (ja) | ソラネシルアミン誘導体の製造方法 | |
| JPS58203950A (ja) | α−アミノメチルベンジルアルコ−ル誘導体の製造法 | |
| Zhou et al. | Observations made in exploring a pyridinium salt photochemical approach to the synthesis of (+)-lactacystin | |
| KR100828032B1 (ko) | 발리올론 유도체의 제조방법 | |
| JPH0470295B2 (en]) | ||
| CN115572289A (zh) | 一种特索芬辛的合成方法 | |
| CN120423954A (zh) | 一种丁-3-炔酸乙酯的合成方法 | |
| JP4366854B2 (ja) | １２−アミノ−４，８−ドデカジエンニトリル及びその製造法 |