# US 5,352,845 A · Process for manufacture of optically active saturated compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,352,845 A - Document ID: US5352845A - Status: Granted - Kind: A - Application number: 08/036,887 - Filed: 1993-03-25 - Granted: 1994-10-04 - Earliest claimed: 1990-02-20 - Assignees: Asahi Denka Kogyo Kabushiki Kaisha - Inventors: Seiichi Takano; Kunio Ogasawara - Web page: https://patentgrep.com/patent/US5352845A ## CPC - C07D 493/04: Ortho-condensed systems - C07C 29/132: by reduction of an oxygen containing functional group - C07C 29/58: by elimination of halogen, e.g. by hydrogenolysis, splitting-off (C07C29/124 takes precedence) - C07C 33/042: with only one triple bond - C07C 37/07: with simultaneous reduction of C=O group in that ring - C07C 41/26: by introduction of hydroxy or O-metal groups - C07C 41/30: by increasing the number of carbon atoms, e.g. by oligomerisation - C07C 46/02: by oxidation giving rise to quinoid structures - C07C 50/28: with monocyclic quinoid structure - C07C 69/007: Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom - C07D 303/08: with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals - C07D 303/14: by free hydroxyl radicals - C07D 303/16: by esterified hydroxyl radicals - C07D 309/08: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms - C07D 309/30: Oxygen atoms, e.g. delta-lactones - C07D 309/32: having two double bonds between ring members or between ring members and non-ring members - C07D 311/58: other than with oxygen or sulphur atoms in position 2 or 4 - C07B 2200/07: Optical isomers - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F) ## Abstract A process for manufacturing an optically active saturated compound of the general formula (25): ##STR1## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22, and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, is disclosed. ## Claims ### Claim 1 A process for manufacturing an optically active saturated compound of the general formula (25): ##STR63## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22 and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, said process comprising the steps of: treating an optically active halogenated compound of the general formula (21b): ##STR64## wherein X.sub.20 represents a halogen atom, with a strong base, to obtain an optically active corresponding acetylene alcohol ##STR65## while retaining the chirality; reacting said optically active acetylene alcohol compound of the formula (21c) with a benzene halide of the general formula (24): ##STR66## wherein X'.sub.20 represents a halogen atom, and R.sub.20, R.sub.21, R.sub.22 and R.sub.23 have the same meanings as above, to obtain an optically active corresponding phenylacetylene compound of the general formula (21d): ##STR67## wherein R.sub.20, R.sub.21, R.sub.22 and R.sub.23 have the same meanings as above, while retaining the chirality; and reducing said optically active phenylacetylene compound of the general formula (21d) to obtain the optically active corresponding saturated compound of the general formula (25) while retaining the chirality. ### Claim 2 (depends on 1) A process according to claim 1, wherein R.sub.20 represents a lower alkyl group having 1 to 4 carbon atoms. ### Claim 3 (depends on 1) A process according to claim 1, wherein each of R.sub.20, R.sub.21, R.sub.22 and R.sub.23 is a methyl group. ### Claim 4 (depends on 1) A process according to claim 1, wherein said strong base is alkali metal alkyl. ### Claim 5 (depends on 1) A process according to claim 1, wherein said halogenated compound of the general formula (21b) is treated under an inert gas. ### Claim 6 (depends on 1) A process according to claim 1, wherein said acetylene alcohol compound of the formula (21c) is reacted with said benezene halide of the general formula (24) in the presence of a palladium catalyst under an inert gas. ### Claim 7 (depends on 6) A process according to claim 6, wherein said reaction is carried out under ultrasonication. ### Claim 8 (depends on 1) A process according to claim 1, wherein said phenylacetylene compound of the formula (21d) is reduced in the presence of platinum oxide by passing hydrogen stream. ### Claim 9 A process for manufacturing an optically active saturated compound of the general formula (25-1): ##STR68## said process comprising the steps of: treating an optically active halogenated compound of the general formula (21b): ##STR69## wherein X.sub.20 represents a halogen atom, with alkali metal alkyl under an inert gas, to obtain an optically active corresponding acetylene alcohol compound of the formula (21c): ##STR70## while retaining the chirality; reacting said optically active acetylene alcohol compound of the formula (21c) with a benzene halide of the formula (24-1): ##STR71## wherein X'.sub.20 represents a halogen atom, in the presence of a palladium catalyst under an inert gas and under ultrasonication, to obtain an optically active corresponding phenylacetylene compound of the formula (21d-1): ##STR72## while retaining the chirality; and reducing said optically active phenylacetylene compound of the general formula (21d) in the presence of platinum oxide by passing hydrogen stream, to obtain the optically active corresponding saturated compound of the general formula (25) while retaining the chirality.