JPS63165348A - Production of optically active 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol - Google Patents
Production of optically active 1-(2,5-dimethoxyphenyl)-2-amino-1-propanolInfo
- Publication number
- JPS63165348A JPS63165348A JP31425886A JP31425886A JPS63165348A JP S63165348 A JPS63165348 A JP S63165348A JP 31425886 A JP31425886 A JP 31425886A JP 31425886 A JP31425886 A JP 31425886A JP S63165348 A JPS63165348 A JP S63165348A
- Authority
- JP
- Japan
- Prior art keywords
- dimethoxyphenyl
- propanol
- amino
- optically active
- acetylleucine
- 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.)
- Granted
Links
- WJAJPNHVVFWKKL-UHFFFAOYSA-N Methoxamine Chemical compound COC1=CC=C(OC)C(C(O)C(C)N)=C1 WJAJPNHVVFWKKL-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 230000003287 optical effect Effects 0.000 claims abstract description 22
- WXNXCEHXYPACJF-ZETCQYMHSA-N N-acetyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(C)=O WXNXCEHXYPACJF-ZETCQYMHSA-N 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 229960000669 acetylleucine Drugs 0.000 claims abstract description 14
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- -1 methanol Chemical compound 0.000 abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 abstract description 2
- 239000003125 aqueous solvent Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- 239000003446 ligand Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 1
- 150000004692 metal hydroxides Chemical class 0.000 abstract 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YGRFXPCHZBRUKP-UHFFFAOYSA-N Methoxamine hydrochloride Chemical compound Cl.COC1=CC=C(OC)C(C(O)C(C)N)=C1 YGRFXPCHZBRUKP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- 125000003440 L-leucyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical compound CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- WXNXCEHXYPACJF-SSDOTTSWSA-N N-acetyl-D-leucine Chemical group CC(C)C[C@H](C(O)=O)NC(C)=O WXNXCEHXYPACJF-SSDOTTSWSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用・分野〉
本発明は光学活性１−（２，５−ジメトキシフェニル）
−２−アミノ−１−プロパノールの製造方法に関する。[Detailed Description of the Invention] <Industrial Application/Field> The present invention relates to optically active 1-(2,5-dimethoxyphenyl)
The present invention relates to a method for producing -2-amino-1-propanol.
〈従来の技術〉
本発明の対象とする光学活性１−（２，５−ジメトキシ
フェニル）−２−アミノ−１−プロパノールは不斉修飾
金属水素化物の不斉配位子として重要な化合物であり（
例えば、特開昭６１−６８４７１号公報）、ラセミ体に
光学分割剤として光学活性酒石酸あるいは光学活性ジベ
ンゾイル酒石酸を作用させることにより光学分割して製
造されることも良く知られている（例えばＪ、Ｍｅｄ、
、 ｌ １（４）８８８（１９６８））。<Prior art> Optically active 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol, which is the subject of the present invention, is an important compound as an asymmetric ligand for asymmetrically modified metal hydrides. (
For example, JP-A No. 61-68471), it is also well known that the racemate is produced by optical resolution by reacting optically active tartaric acid or optically active dibenzoyltartaric acid as an optical resolution agent (for example, J, Med,
, l 1(4) 888 (1968)).
〈発明が解決しようとする問題点〉
しかしながら、光学分割剤として酒石酸、ジベンゾイル
酒石酸を用いる従来法では煩雑な操作を必要とするのみ
ならず、得られたものの光学純度が約６０％程度と充分
ではなく、高い先約な問題点を有していた。<Problems to be solved by the invention> However, the conventional method using tartaric acid or dibenzoyltartaric acid as an optical resolving agent not only requires complicated operations, but also has an insufficient optical purity of about 60%. However, there were problems with high prior commitments.
く問題点を解決するための手段〉
本発明者らはこのような状況に鑑み、より効率的な光学
活性１−（２，５−ジメトキシフェニル）−２−アミノ
−１−プロパノールの製造方法を見い出すべく税１コ検
討を重ねた結果、光学分割剤として光学活性Ｎ−アセチ
ルロイシンという特定の化合物を用いれば極めて簡単な
操作で容易にしかも高い光学純度で目的物が得られるこ
とを見い出すとともに、さらに柚々の検討を加え、本％
明を完成した。Means for Solving the Problems In view of the above circumstances, the present inventors have developed a more efficient method for producing optically active 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol. As a result of repeated studies in order to find this, we discovered that by using a specific compound called optically active N-acetylleucine as an optical resolving agent, the desired product could be easily obtained with extremely simple operations and with high optical purity. After further consideration, this%
Completed Ming.
すなわち本発明は−−１−（２，５−ジメトキシフェニ
ル）−２−アミノ−１−プロパノールを光学分割して光
学活性１−（２，５−ジメトキシフェニル）−２−アミ
ノ−１−プロパノールを製造する方法において、光学分
割剤として光学活性Ｎ−アセチルロイシンを用いること
を特徴とする光学活性１−（２，５−ジメトキシフェニ
ル）−２−アミノ−１−プロパノールの工業的に優れた
製造方法を提供するものである。That is, the present invention optically resolves 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol to obtain optically active 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol. An industrially excellent method for producing optically active 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol, the method comprising using optically active N-acetylleucine as an optical resolution agent. It provides:
本発明の被分割剤である１−（２，５−ジメトキシフェ
ニル）−２−アミノ−１−プロパノールは、その１位お
よび２位に２＠の不斉炭素原子が存在することから、エ
リスロ型とスレオ型の立体異性体が存在するが、エリス
ロ型を用いるのが好ましい。これ等は鉱酸塩、例えば塩
酸塩、硫酸塩であっても使用できる。1-(2,5-dimethoxyphenyl)-2-amino-1-propanol, which is the resolving agent of the present invention, has an erythro-type Although there are stereoisomers of the and threo type, it is preferable to use the erythro type. These can also be used in the form of mineral acid salts, such as hydrochlorides and sulfates.
ν１
また光学分叢剤である光学活性Ｎ−アセチルロイシンと
してはＬ一体またはＤ一体が用いられる。その被分割剤
に対する使用量は被分割剤の光学純度によっても若干変
動するが、例えば、Ｄ一体とＬ一体の等量混合物であｄ
≧ミ体の場合は、通常等モル程度用いられるが、０．５
モル倍程度まで削減することもできる。ν1 In addition, as the optically active N-acetylleucine which is an optical plexus agent, L-unit or D-unit is used. The amount used for the agent to be separated varies slightly depending on the optical purity of the agent to be separated, but for example, if a mixture of equal amounts of D and L is used, d
In the case of ≧mi-form, approximately equimolar amount is usually used, but 0.5
It can also be reduced to about twice the mole.
光学分割せしめるに当り、遊離の被分割剤を用いる場合
は遊離の光学活性Ｎ−アセチルロイシンを、被分割剤が
鉱酸塩である場合は該Ｎ−アセチルロイシンのアルカリ
塩、例えばナトリウム塩、カリウム塩などを通常作用さ
せる。For optical resolution, if a free resolving agent is used, free optically active N-acetylleucine is used, and if the resolving agent is a mineral salt, an alkali salt of the N-acetylleucine, such as a sodium salt or a potassium salt, is used. Usually treated with salt, etc.
また光学分割の際に用いられる溶媒としては。Also, as a solvent used during optical resolution.
例えば水、メタノール、エタノール等の低級アルコール
、アセトン等の脂肪族低級ケトンなどの有機溶媒を含有
する水性溶媒が挙げられる。Examples include water, aqueous solvents containing organic solvents such as lower alcohols such as methanol and ethanol, and aliphatic lower ketones such as acetone.
光学分割は例えば、上記溶媒中で被分割剤と光学活性Ｎ
−アセチルロイシンを室温乃至加温下に攪拌あるいは静
置することにより実施できる。For optical resolution, for example, the agent to be resolved and the optically active N
- This can be carried out by stirring or leaving acetylleucine at room temperature or under heating.
ここで光学分割剤としてＮ−アセチルロイシンのし一体
を用いた場合には、１−（２，５−ジメトキシフェニル
）−２−アミノ−１−プロパノールの（−）一体とＮ−
アセチル−Ｌ−ロイシンの塩が難溶性のジアステレオマ
ーとして、また（＋）一体とＮ−アセチル−Ｌ−ロイシ
ンの塩が易谷性のジアステレオマーとして得られる。When N-acetylleucine monomer is used as an optical resolving agent, the (-) monomer of 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol and N-
A salt of acetyl-L-leucine is obtained as a poorly soluble diastereomer, and a salt of (+) and N-acetyl-L-leucine is obtained as a diastereomer that is easily soluble.
一方、光学分割剤としてＮ−アセチルロイシンのＤ一体
を用いた場合には、（＋）一体とＮ−アセチル−Ｄ−ロ
イシンの塩が難溶性のジアステレオマーとして、（−）
一体と−Ｎ−アセチルーＤ−ロイシンの塩が易谷性のジ
アステレオマーとして得られる。On the other hand, when N-acetylleucine D monomer is used as an optical resolution agent, the (+) monomer and N-acetyl-D-leucine salt form a poorly soluble diastereomer (-)
A salt of -N-acetyl-D-leucine is obtained as a simple diastereomer.
かくして得られるジアステレオマーは、例えば水酸化ナ
トリウム、水酸化カリウム等のアルカリにより容易に分
解され、トルエン、ジエチルエーテル、クロロホルム等
の有機溶媒で抽出することにより、万機層から高純度の
光学活性１−（２，５−ジメトキシフェニル）−２−ア
ミノ−１−プロパノールが得られる。The diastereomers thus obtained are easily decomposed by alkalis such as sodium hydroxide and potassium hydroxide, and extracted with organic solvents such as toluene, diethyl ether, and chloroform to obtain highly purified optically active diastereomers from the manki layer. 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol is obtained.
一方、有機溶媒で抽出した残りの水層を塩酸、硫酸等の
鉱酸で酸性にすることにより、光学活性Ｎ−アセチルロ
イシンが結晶として析出する。On the other hand, by acidifying the remaining aqueous layer extracted with an organic solvent with a mineral acid such as hydrochloric acid or sulfuric acid, optically active N-acetylleucine is precipitated as crystals.
かかる結晶をＰ別することにより、ラセミ化することな
しに光学活性Ｎ−アセチルロイシンが回収することがで
き、このものは光学分割剤として再使用することができ
る。By separating such crystals with P, optically active N-acetylleucine can be recovered without racemization, and this can be reused as an optical resolution agent.
〈発明の消果〉
本発明の方法は従来の光学活性１−（２，５−ジメトキ
シフェニル）−２−アミノ−１−プロパノールの一製造
に比し、純度、収率の両面において遥かに優れ、しかも
操作が容易であるこトカラ特に工業的製造として有用で
ある。<Results of the invention> The method of the present invention is far superior in both purity and yield compared to the conventional production of optically active 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol. Moreover, since it is easy to operate, it is particularly useful for industrial production.
〈実施例〉
以下、実施例により本発明をさらに詳細に説明するが、
本発明はこれらに限定されるものではない。<Example> The present invention will be explained in more detail with reference to Examples below.
The present invention is not limited to these.
実施例１．（至）−エリスロー１−（２，５−ジメトキ
シフェニル）−２−アミノ−１−プロパノール塩酸塩１
．２４ｙ（５ミリモル）の水２〇−溶液にＮ−アセチル
−Ｌ−ロイシン０．８６６２（５ミリモル）の０．５Ｎ
−カセイソーダ１０−溶液を室温で加え６時間静置する
と（−）−エリスロー１−（２，５−ジメトキシフェニ
ル）−２−アミノ−１−プロパノールのＮ−アセチル−
Ｌ−ロイシン塩の結晶が析出した。結晶を炉取すると０
．４７Ｆが得られた。Example 1. (To)-Erythro 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol hydrochloride 1
．． 0.5N of N-acetyl-L-leucine 0.8662 (5 mmol) in a 20-solution of 24y (5 mmol) in water.
- When a solution of caustic soda 10- was added at room temperature and allowed to stand for 6 hours, the N-acetyl-
Crystals of L-leucine salt were precipitated. When the crystal is removed by furnace, it becomes 0.
．． 47F was obtained.
〔α〕廿−８０．６６°（Ｃ０，８０，水）次にカセイ
ソーダ水溶液を加えて分解し、クロロホルムで抽出する
と０．２５６Ｆの←）−エリスロー１−（２，５−ジメ
トキシフェニル）−２−アミノ−１−プロパノールが得
られた。[α] -80.66° (C0,80, water) Next, add an aqueous solution of caustic soda to decompose, and extract with chloroform to obtain 0.256F←)-Erythro 1-(2,5-dimethoxyphenyl)-2 -Amino-1-propanol was obtained.
〔α）”−２７，５９°＜ Ｃｔｏ 、水）（ＨＣｌ塩
）糖誘導体のジアステレオマーに導き、高速液体クロマ
トグラフィーで光学純度を分析すると９６．７％であっ
た。[α)''-27,59°<Cto, water) (HCl salt) The diastereomer of the sugar derivative was derived, and the optical purity was analyzed by high performance liquid chromatography and found to be 96.7%.
実施例２．（ト）−エリスロー１−（２，５−ジメトキ
シフェニル）−２−アミノ−１−プロパノール塩酸塩１
．２４ｙ（５ミリモル）の水１５−溶液にＮ−アセチル
−Ｌ−ロイシン０．４８８９＜２・５ミリモル）の０．
５Ｎ−カセイソーダ５ｍｊ溶液を室温で加え５時間静置
すると（−）−エリスロー１−（２，５−ジメトキシフ
ェニル）−２−アミノ−１−プロパノールのＮ−アセチ
ル−Ｌ−ロイシン塩の結晶が析出した。結晶をＰ取する
と０．８５４Ｆが得られた。Example 2. (t)-Erythro 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol hydrochloride 1
．． 0.4889<2.5 mmol) of N-acetyl-L-leucine in a 15-solution of 24y (5 mmol) in water.
Add 5mj of 5N caustic soda solution at room temperature and leave it for 5 hours to precipitate crystals of N-acetyl-L-leucine salt of (-)-erythro 1-(2,5-dimethoxyphenyl)-2-amino-1-propanol. did. When P was removed from the crystal, 0.854F was obtained.
（＝ｇ）甘−８１，２９°（Ｃ０，８５，水）次に、カ
セイソーダ水溶液で分解し、クロロホルムで抽出すると
０．１９１ ｆ！の（−）−エリスロー１−（２，５−
ジメトキシフェニル）−２−アミノ−１−プロパノール
が得られた。(=g) Sweet -81,29° (C0,85, water) Next, it is decomposed with aqueous caustic soda solution and extracted with chloroform to give 0.191 f! (-)-Erythro 1-(2,5-
Dimethoxyphenyl)-2-amino-1-propanol was obtained.
実施例１と同様に光学純度を分析すると９７．０％であ
った。The optical purity was analyzed in the same manner as in Example 1 and found to be 97.0%.
Claims (1)
ミノ−１−プロパノールを光学分割して光学活性１−（
２，５−ジメトキシフェニル）−２−アミノ−１−プロ
パノールを製造する方法において、光学分割剤として光
学活性Ｎ−アセチルロイシンを用いることを特徴とする
光学活性１−（２，５−ジメトキシフェニル）−２−ア
ミノ−１−プロパノールの製造方法。(±)-1-(2,5-dimethoxyphenyl)-2-amino-1-propanol was optically resolved and optically active
Optically active 1-(2,5-dimethoxyphenyl)-2,5-dimethoxyphenyl)-2-amino-1-propanol is produced by using optically active N-acetylleucine as an optical resolving agent. -A method for producing 2-amino-1-propanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61314258A JPH0667883B2 (en) | 1986-12-26 | 1986-12-26 | Process for producing optically active 1- (2,5-dimethoxyphenyl) -2-amino-1-propanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61314258A JPH0667883B2 (en) | 1986-12-26 | 1986-12-26 | Process for producing optically active 1- (2,5-dimethoxyphenyl) -2-amino-1-propanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63165348A true JPS63165348A (en) | 1988-07-08 |
| JPH0667883B2 JPH0667883B2 (en) | 1994-08-31 |
Family
ID=18051184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61314258A Expired - Lifetime JPH0667883B2 (en) | 1986-12-26 | 1986-12-26 | Process for producing optically active 1- (2,5-dimethoxyphenyl) -2-amino-1-propanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0667883B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010501487A (en) * | 2006-08-18 | 2010-01-21 | シェーリング コーポレイション | Resolution process of chiral piperidine alcohol and synthesis process of pyrazolo- [1,5] -pyrimidine derivatives using piperidine alcohol |
| JP2011514341A (en) * | 2008-02-27 | 2011-05-06 | クラリアント・スペシャルティ・ファイン・ケミカルズ（フランス） | Process for producing optically active α-aminoacetals |
-
1986
- 1986-12-26 JP JP61314258A patent/JPH0667883B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF THE TENNESSEE ACADEMY OF SCIENCE=1974 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010501487A (en) * | 2006-08-18 | 2010-01-21 | シェーリング コーポレイション | Resolution process of chiral piperidine alcohol and synthesis process of pyrazolo- [1,5] -pyrimidine derivatives using piperidine alcohol |
| JP2011514341A (en) * | 2008-02-27 | 2011-05-06 | クラリアント・スペシャルティ・ファイン・ケミカルズ（フランス） | Process for producing optically active α-aminoacetals |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0667883B2 (en) | 1994-08-31 |
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