http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-889774-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_3395c5cb958d81965344886b0ca92581 |
| filingDate | 1958-10-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1962-02-21-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-889774-A |
| titleOfInvention | Improvements in or relating to yohimbane derivatives |
| abstract | The invention comprises 9; 10-benzodeserpidine of the formula p <FORM:0889774/IV (b)/1> dextro - rotary 18b - acetoxy - 9, 10 - benzo - 17a - methoxy - 16b - methoxycarbonyl - D 3(14) - 20a - yohimbene, laevo - rotatory 18b - acetoxy - 9,10-benzo-17a - methoxy - 16b -methoxycarbonyl - 3b , 20a -yohimbane, its 3a -epimer and its 18b -hydroxy analogue, together with a process for their preparation by reacting the methyl ester of 1b - carboxymethyl - 2b - methoxycarbonyl - 3a - methoxy-4b -acetoxy-6b -formyl cyclohexane with 4,5-benzotryptamine in an inert solvent, reducing the resultant methyl ester of 18b -acetoxy-9,10-benzo - 17a - methoxy - 16b - methoxycarbonyl - 2 : 3,3 : 4-diseco-D 4(21)-20a -yohimbene-3-oic acid with a metal borohydride to yield dextro-rotary 9, 10 - benzo - 18b - hydroxy - 17a - methoxy - 16b - methoxycarbonyl - 3 - oxo - 2 : 3 - seco - 20a -yohimbane which is acetylated to the laevorotatory 18b -acetoxy derivative, cyclizing the latter by dehydration (e.g. with phosphorus oxychloride) to give dextro-rotary 18b -acetoxy-9, 10 - benzo - 17a - methoxy - 16b - methoxy - carbonyl-D 3(14)-20a -yohimbene (I), reducing the last mentioned compound with a metal/acid reducing system, preferably with zinc and formic acid, to laevo-rotary 18b -acetoxy-9,10-benzo-17a - methoxy - 16b - methoxycarbonyl - 3b , 20a - yohimbane, partially saponifying and then trimethoxybenzoylating the resulting laevo-rotatory 9, 10 - benzo - 18b - hydroxy - 17a - methoxy - 16b - methoxycarbonyl - 3b , 20a - yohimbane to give laevo-rotatory 9,10-benzo deserpidine. Reduction of I with sodium borohydride yields the epimeric 3a ,20a -yohimbane. Detailed examples are given. Specifications 862,611, 868,475 and 888,411 are referred to. |
| priorityDate | 1957-10-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 26.