JPH0470305B2 - - Google Patents
Info
- Publication number
- JPH0470305B2 JPH0470305B2 JP14533788A JP14533788A JPH0470305B2 JP H0470305 B2 JPH0470305 B2 JP H0470305B2 JP 14533788 A JP14533788 A JP 14533788A JP 14533788 A JP14533788 A JP 14533788A JP H0470305 B2 JPH0470305 B2 JP H0470305B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenylpropylamine
- optically active
- salt
- solvent
- 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
Links
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 description 13
- WECUIGDEWBNQJJ-SECBINFHSA-N (2r)-4-phenylbutan-2-amine Chemical compound C[C@@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-SECBINFHSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WECUIGDEWBNQJJ-VIFPVBQESA-N (2s)-4-phenylbutan-2-amine Chemical compound C[C@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-VIFPVBQESA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229960004452 methionine Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XUYPXLNMDZIRQH-ZCFIWIBFSA-N N-acetyl-D-methionine Chemical compound CSCC[C@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-ZCFIWIBFSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 1-methyl-3-phenylpropylamine Amine Chemical class 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- XAKITKDHDMPGPW-PHDIDXHHSA-N [(3r,4r)-4-acetyloxy-2,5-dioxooxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1[C@@H](OC(C)=O)C(=O)OC1=O XAKITKDHDMPGPW-PHDIDXHHSA-N 0.000 description 1
- IDVJXKFJHUNVNB-UHFFFAOYSA-N acetonitrile;n-ethylethanamine Chemical compound CC#N.CCNCC IDVJXKFJHUNVNB-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- MLHBZVFOTDJTPK-UHFFFAOYSA-N n-methyl-3-phenylpropan-1-amine Chemical compound CNCCCC1=CC=CC=C1 MLHBZVFOTDJTPK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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−メチル−３−フエニル
プロピルアミンの製造法に関するものである。Detailed Description of the Invention <Industrial Field of Application> The present invention relates to a method for producing optically active 1-methyl-3-phenylpropylamine.
＜従来の技術＞
光学活性１−メチル−３−フエニルプロピルア
ミンは、β−ブロツカー剤などの医薬品の合成原
料として有用な化合物であるが、化学的に合成さ
れた１−メチル−フエニルプロピルアミンは、
RS体であるので前記合成原料とするには光学分
割して光学活性なものにしなければならない。１
−メチル−３−フエニルプロピルアミンの光学活
性分割方法として、シス樟脳酸無水物を用いる方
法（Aust.J.Chem.、34、(3)665−670 1981）、
（2R、3R）−２，３−ジアセトキシコハク酸無水
物を用いる方法（Aust.J.Chem.、32、(2)2625−
2629（1979））が知られている。<Prior art> Optically active 1-methyl-3-phenylpropylamine is a compound useful as a synthetic raw material for pharmaceuticals such as β-blocker agents, but chemically synthesized 1-methyl-3-phenylpropylamine Amine is
Since it is an RS form, it must be optically resolved to make it optically active in order to use it as the synthetic raw material. 1
-A method for optically active resolution of methyl-3-phenylpropylamine using cis-camphoric anhydride (Aust.J.Chem., 34 , (3)665-670 1981),
Method using (2R, 3R)-2,3-diacetoxysuccinic anhydride (Aust.J.Chem., 32 , (2)2625-
2629 (1979)) is known.
＜発明が解決しようとする課題＞
しかし、前記の両方法は収率が低い上に光学純
度も低く、工業的に実用化可能なレベルではな
い。そこで、本発明者らは、光学活性１−メチル
−３−フエニルプロピルアミンの実用的な製造法
の確立を目的として鋭意検討をかさねた。<Problems to be Solved by the Invention> However, both of the above methods have low yields and low optical purity, and are not at a level that is industrially practical. Therefore, the present inventors conducted extensive studies with the aim of establishing a practical method for producing optically active 1-methyl-3-phenylpropylamine.
＜課題を解決するための手段＞
その結果、上記目的は
式
（式中、Ｒはフエニル基またはメチル基を表わ
す。）
で示される光学活性Ｎ−アシルメチオニンを分割
剤として、（RS）−１−メチル−３−フエニルプ
ロピルアミンを分割することによつて達成される
ことがわかつた。<Means to solve the problem> As a result, the above purpose is the formula (In the formula, R represents a phenyl group or a methyl group.) By resolving (RS)-1-methyl-3-phenylpropylamine using an optically active N-acylmethionine represented by the following as a resolving agent: I found out that it can be achieved.
すなわち、本発明は
次の一般式（）
（式中、Ｒはフエニル基またはメチル基を表わ
す。）
で示される光学活性Ｎ−アシルメチオニンを分割
剤として、（RS）−１−メチル−３−フエニルプ
ロピルアミンを光学分割することを特徴とする光
学活性１−メチル−３−フエニルプロピルアミン
の製造法である。 That is, the present invention is based on the following general formula () (In the formula, R represents a phenyl group or a methyl group.) (RS)-1-Methyl-3-phenylpropylamine is optically resolved using an optically active N-acylmethionine represented by the following as a resolving agent. This is a method for producing optically active 1-methyl-3-phenylpropylamine.
以下、本発明の構成を詳しく説明する。 Hereinafter, the configuration of the present invention will be explained in detail.
本発明で用いる分割剤は
次の一般式（）
（式中、Ｒはフエニル基またはメチル基を表わ
す。）
で示される光学活性Ｎ−アシルメチオニンであ
り、そのＤ体およびＬ体のいずれも用いることが
できる。 The resolving agent used in the present invention has the following general formula () (In the formula, R represents a phenyl group or a methyl group.) It is an optically active N-acylmethionine represented by the following formula, and both its D-form and L-form can be used.
本発明において、原料として用いられる（RS）
−１−メチル−３−フエニルプロピルアミンは、
（Ｒ）−１−メチル−３−フエニルプロピルアミン
と（Ｓ）−１−メチル−３−フエニルプロピルア
ミンとを等量含むラセミ型混合物のみならず、い
ずれか一方の光学異性体を等量以上に含む混合物
をも包含するものである。 In the present invention, (RS) used as a raw material
-1-methyl-3-phenylpropylamine is
Not only a racemic mixture containing equal amounts of (R)-1-methyl-3-phenylpropylamine and (S)-1-methyl-3-phenylpropylamine, but also an equal amount of one of the optical isomers. It also includes mixtures containing more than the same amount.
（RS）−１−メチル−３−フエニルプロピルア
ミンの光学分割は次の手順と条件で行なう。 Optical resolution of (RS)-1-methyl-3-phenylpropylamine is carried out under the following procedure and conditions.
まず、溶媒中で（RS）−１−メチル−３−フエ
ニルプロピルアミン１モルに対して0.1〜2.0モ
ル、好ましくは0.5〜1.0モル量のＮ−アシル−Ｄ
−メチオニンもしくはＮ−アシル−Ｌ−メチオニ
ンを接触させる。 First, in a solvent, an amount of N-acyl-D of 0.1 to 2.0 mol, preferably 0.5 to 1.0 mol, per 1 mol of (RS)-1-methyl-3-phenylpropylamine.
- Contacting methionine or N-acyl-L-methionine.
ここで使用する溶媒としては、１−メチル−３
−フエニルプロピルアミンとＮ−アシルメチオニ
ンを溶解するとともに溶液中でこれらの化合物を
化学的に変質せしめることなく、かつジアステレ
オマー塩を析出せしめるものであればよく、たと
えば、水、メタノール、エタノール、プロパノー
ルなどの低級アルコール、アセトンまたはこれら
の混合溶媒を用いることができる。好ましい溶媒
は、水、低級アルコールであり、特に水がもつと
も好ましく用いられる。 The solvent used here is 1-methyl-3
- Any material that dissolves phenylpropylamine and N-acylmethionine, does not chemically alter these compounds in solution, and precipitates diastereomeric salts may be used, such as water, methanol, and ethanol. , a lower alcohol such as propanol, acetone, or a mixed solvent thereof can be used. Preferred solvents are water and lower alcohols, with water being particularly preferred.
（RS）−１−メチル−３−フエニルプロピルア
ミンに前記分割剤を接触させる方法としては、上
記した溶媒中に（RS）−１−メチル−３−フエニ
ルプロピルアミンおよび分割剤を別個に溶解して
混合してもよいし、また溶媒中にそれらを順次溶
解してもよい。さらにあらかじめ（RS）−１−メ
チル−３−フエニルプロピルアミンと分割剤とか
らつくつた塩を該溶媒中に添加溶解してもよい。 As a method for bringing the resolving agent into contact with (RS)-1-methyl-3-phenylpropylamine, (RS)-1-methyl-3-phenylpropylamine and the resolving agent are separately added to the above-mentioned solvent. They may be dissolved and mixed, or they may be sequentially dissolved in a solvent. Furthermore, a salt prepared from (RS)-1-methyl-3-phenylpropylamine and a resolving agent may be added and dissolved in the solvent in advance.
次に、接触によつて得られた溶液を冷却およ
び／あるいは濃縮する。すると、難溶性のジアス
テレオマー塩（（Ｒ）−１−メチル−３−フエニル
プロピルアミン・Ｎ−アシル−Ｄ−メチオニン塩
もしくは（Ｓ）−１−メチル−３−フエニルプロ
ピルアミン・Ｎ−アシル−Ｌ−メチオニン塩）が
晶析する。難溶性のジアステレオマー塩を分割溶
媒から析出させる際の温度は使用する溶媒の凝固
点から沸点の範囲であればよく、目的に応じて適
宜決められるが、通常０℃から80℃の範囲で十分
である。 Next, the solution obtained by contacting is cooled and/or concentrated. Then, a sparingly soluble diastereomeric salt ((R)-1-methyl-3-phenylpropylamine/N-acyl-D-methionine salt or (S)-1-methyl-3-phenylpropylamine/N -acyl-L-methionine salt) crystallizes. The temperature at which a poorly soluble diastereomer salt is precipitated from the splitting solvent may range from the freezing point to the boiling point of the solvent used, and can be determined as appropriate depending on the purpose, but a range of 0°C to 80°C is usually sufficient. It is.
難溶性のジアステレオマー塩の結晶は、過、
遠心分離などの通常の固液分離法によつて容易に
分離することができる。 Crystals of poorly soluble diastereomeric salts can be obtained by
It can be easily separated by conventional solid-liquid separation methods such as centrifugation.
一方、難溶性のジアステレオマー塩を分離した
残りの母液をそのまま、または濃縮および／ある
いは冷却して易溶性のジアステレオマー塩（（Ｒ）
−１−メチル−３−フエニルプロピルアミン・Ｎ
−アシル−Ｌ−メチオニン塩もしくは（Ｓ）−１
−メチル−３−フエニルプロピルアミン・Ｎ−ア
シル−Ｄ−メチオニン塩）を析出せしめ、これを
分離することもできる。 On the other hand, the remaining mother liquor from which the poorly soluble diastereomeric salts have been separated can be used as is or concentrated and/or cooled to obtain easily soluble diastereomeric salts ((R)
-1-methyl-3-phenylpropylamine/N
-Acyl-L-methionine salt or (S)-1
-Methyl-3-phenylpropylamine/N-acyl-D-methionine salt) can also be precipitated and separated.
かくして得られる各ジアステレオマー塩を適当
な方法で分離することによつて、分割剤と（Ｒ）
−１−メチル−３−フエニルプロピルアミンまた
は（Ｓ）−１−メチル−３−フエニルプロピルア
ミンを分離・採取することができる。 By separating each diastereomer salt obtained in this way by an appropriate method, the resolving agent and (R) are separated.
-1-Methyl-3-phenylpropylamine or (S)-1-methyl-3-phenylpropylamine can be separated and collected.
ジアステレオマー塩の分解方法は任意であり、
たとえば、水性溶媒中酸またはアルカリで処理す
る方法などが適用できる。すなわち、たとえばジ
アステレオマー塩水溶液にアンモニアを添加し、
これをクロロホルムなどの有機溶媒で抽出すると
（Ｒ）−１−メチル−３−フエニルプロピルアミン
または（Ｓ）−１−メチル−３−フエニルプロピ
ルアミンが有機溶媒相に抽出されてくるので、抽
出後有機溶媒を留出することによつて容易に光学
活性１−メチル−３−フエニルプロピルアミンを
得ることができる。 The method for decomposing diastereomeric salts is arbitrary;
For example, a method of treatment with acid or alkali in an aqueous solvent can be applied. That is, for example, by adding ammonia to an aqueous diastereomeric salt solution,
When this is extracted with an organic solvent such as chloroform, (R)-1-methyl-3-phenylpropylamine or (S)-1-methyl-3-phenylpropylamine is extracted into the organic solvent phase. Optically active 1-methyl-3-phenylpropylamine can be easily obtained by distilling off the organic solvent after extraction.
＜実施例＞
以下、実施例により本発明を具体的に説明す
る。<Example> Hereinafter, the present invention will be specifically explained with reference to Examples.
なお、実施例中、光学純度は次のように測定し
たものを示す。 In addition, in the examples, the optical purity is measured as follows.
光学純度：１−メチル−３−フエニルプロピルア
ミンまたはジアステレオマー塩の0.2％水／ア
ルコール溶液を調製し、２％トリエチルアミン
のアセトニトリル溶液0.1mlと0.4％２、３、
４、６−テトラ−ｏ−アセチル−β−Ｄ−グル
コピラノシルイソチオシアネート（GITC）の
アセトニトリル溶液0.1mlとを添加して混合し
た。30分室温で反応させたのち、0.3％ジエチ
ルアミンのアセトニトル溶液で過剰のGITCを
分解したサンプルを次のHPLC条件で分析し、
アミンの光学純度（％e.e.）を求めた。Optical purity: Prepare a 0.2% water/alcohol solution of 1-methyl-3-phenylpropylamine or diastereomeric salt, add 0.1 ml of 2% triethylamine solution in acetonitrile and 0.4% 2,3,
0.1 ml of an acetonitrile solution of 4,6-tetra-o-acetyl-β-D-glucopyranosylisothiocyanate (GITC) was added and mixed. After reacting for 30 minutes at room temperature, excess GITC was decomposed with a 0.3% diethylamine acetonitrile solution, and the sample was analyzed under the following HPLC conditions.
The optical purity (%ee) of the amine was determined.
HPLC条件
カラム：μ−Bondaspnere5μC18−100Å3.9×150
mm
移動相：0.05％H3PO4／メタノール＝53／47 1.1
ml／min
カラムＴ：40℃
UV：254nｍ
保持時間：(R)−１−メチル−３−フエニルプロピ
ルアミンをGITCで誘導体化した化合物
47.8min
(S)−１−メチル−３−フエニルプロピルアミン
をGITCで誘導体化した化合物51.3min
実施例 １
（RS）−１−メチル−３−フエニルプロピルア
ミン4.48ｇとＮ−アセチル−Ｄ−メチオニン5.73
ｇとを水40mlに53℃で加熱溶解した。ゆつくり撹
拌しながら冷却し、４時間後29℃で析出結晶を
別、乾燥して3.65ｇの白色の(R)−１−メチル−３
−フエニルプロピルアミン・Ｎ−アセチル−Ｄ−
メチオニン塩を得た。用いた(R)−１−メチル−３
−フエニルプロピルアミンの量に対しての収率は
71％であつた。得られた結晶の全量を水９mlに溶
解し、28％アンモニア水2.2mlを加えて、クロロ
ホルム10mlで３回抽出した。クロロホルム層は、
飽和硫酸ナトリウム水10mlで洗浄したのち無水硫
酸ナトリウムで乾燥し、溶媒を留出して、1.56ｇ
の(R)−１−メチル−３−フエニルプロピルアミン
（収率95％対塩、光学純度76％e.e.）を得た。HPLC condition column: μ-Bondaspnere5μC 18 −100Å3.9×150
mm Mobile phase: 0.05% H 3 PO 4 /methanol = 53/47 1.1
ml/min Column T: 40℃ UV: 254nm Retention time: Compound of (R)-1-methyl-3-phenylpropylamine derivatized with GITC
47.8min (S)-1-Methyl-3-phenylpropylamine derivatized with GITC 51.3min Example 1 (RS)-1-methyl-3-phenylpropylamine 4.48g and N-acetyl-D -Methionine 5.73
g was dissolved in 40 ml of water by heating at 53°C. Cool slowly with stirring, separate the precipitated crystals at 29°C after 4 hours, and dry to obtain 3.65 g of white (R)-1-methyl-3.
-Phenylpropylamine/N-acetyl-D-
Methionine salt was obtained. (R)-1-methyl-3 used
-The yield relative to the amount of phenylpropylamine is
It was 71%. The entire amount of the obtained crystals was dissolved in 9 ml of water, 2.2 ml of 28% aqueous ammonia was added, and the mixture was extracted three times with 10 ml of chloroform. The chloroform layer is
After washing with 10ml of saturated sodium sulfate water, drying with anhydrous sodium sulfate and distilling off the solvent, 1.56g
(R)-1-methyl-3-phenylpropylamine (yield 95% vs. salt, optical purity 76%ee) was obtained.
実施例 ２
（RS）−１−メチル−３−フエニルプロピルア
ミン3.1ｇとＮ−ベンゾイル−Ｄ−メチルオニン
5.07ｇとを水60mlに50℃で加熱溶解した。ゆつく
り撹拌しながら冷却し、４時間後15℃で析出結晶
を別、乾燥して1.99ｇの白色の(R)−１−メチル
−３−フエニルプロピルアミン・Ｎ−ベンゾイル
−Ｄ−メチルオニン塩を得た。用いた(R)−１−メ
チル−３−フエニルプロピルアミンに対しての収
率は49％であつた。実施例１と同様に処理して、
0.7ｇの(R)−１−メチル−３−フエニルプロピル
アミン（収率95％対塩、光学純度65％e.e.）を得
た。Example 2 3.1 g of (RS)-1-methyl-3-phenylpropylamine and N-benzoyl-D-methylonine
5.07g was dissolved in 60ml of water by heating at 50°C. Cool with gentle stirring, and after 4 hours separate the precipitated crystals at 15°C and dry to obtain 1.99 g of white (R)-1-methyl-3-phenylpropylamine/N-benzoyl-D-methylonine salt. I got it. The yield was 49% based on the (R)-1-methyl-3-phenylpropylamine used. Treated in the same manner as in Example 1,
0.7 g of (R)-1-methyl-3-phenylpropylamine (95% yield vs. salt, optical purity 65% ee) was obtained.
＜発明の効果＞
かくして、本発明によれば、（RS）−１−メチ
ル−３−フエニルプロピルアミンを極めて簡単な
方法で収率よく、高い光学純度で光学分割するこ
とができる。また、分割剤の光学活性Ｎ−アシル
メチオニンは、ジアステレオマー塩を酸・アルカ
リで処理することにより容易に回収でき、さらに
回収された光学活性Ｎ−アシルメチオニンは、再
使用が可能である。<Effects of the Invention> Thus, according to the present invention, (RS)-1-methyl-3-phenylpropylamine can be optically resolved with high yield and high optical purity using an extremely simple method. Further, the optically active N-acylmethionine of the resolving agent can be easily recovered by treating the diastereomer salt with an acid or alkali, and the recovered optically active N-acylmethionine can be reused.
Claims (1)
す。） で示される光学活性Ｎ−アシルメチオニンを分割
剤として、（RS）−１−メチル−３−フエニルプ
ロピルアミンを光学分割することを特徴とする、
光学活性１−メチル−３−フエニルプロピルアミ
ンの製造法。[Claims] First-order general formula () (In the formula, R represents a phenyl group or a methyl group.) (RS)-1-Methyl-3-phenylpropylamine is optically resolved using an optically active N-acylmethionine represented by the following as a resolving agent. and
A method for producing optically active 1-methyl-3-phenylpropylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14533788A JPH023627A (en) | 1988-06-13 | 1988-06-13 | Production of optically active 1-methyl-3-phenylpropylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14533788A JPH023627A (en) | 1988-06-13 | 1988-06-13 | Production of optically active 1-methyl-3-phenylpropylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH023627A JPH023627A (en) | 1990-01-09 |
| JPH0470305B2 true JPH0470305B2 (en) | 1992-11-10 |
Family
ID=15382841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14533788A Granted JPH023627A (en) | 1988-06-13 | 1988-06-13 | Production of optically active 1-methyl-3-phenylpropylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH023627A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2927900B1 (en) * | 2008-02-27 | 2010-09-17 | Clariant Specialty Fine Chem | PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE ALPHA-AMINOACETALS |
-
1988
- 1988-06-13 JP JP14533788A patent/JPH023627A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH023627A (en) | 1990-01-09 |
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