JPH01254658A - Novel pyrrolidinone and production thereof - Google Patents
Novel pyrrolidinone and production thereofInfo
- Publication number
- JPH01254658A JPH01254658A JP8363088A JP8363088A JPH01254658A JP H01254658 A JPH01254658 A JP H01254658A JP 8363088 A JP8363088 A JP 8363088A JP 8363088 A JP8363088 A JP 8363088A JP H01254658 A JPH01254658 A JP H01254658A
- Authority
- JP
- Japan
- Prior art keywords
- benzyl
- pyrrolidinone
- hydroxybutyrate
- hydroxy
- formula
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title claims 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- OGAWUYQBXWYIJM-UHFFFAOYSA-N 1-benzyl-4-hydroxypyrrolidin-2-one Chemical compound O=C1CC(O)CN1CC1=CC=CC=C1 OGAWUYQBXWYIJM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 239000005456 alcohol based solvent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- -1 inorganic acid salts Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZAJNMXDBJKCCAT-UHFFFAOYSA-N ethyl 4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)CCl ZAJNMXDBJKCCAT-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WMRINGSAVOPXTE-UHFFFAOYSA-N methyl 4-chloro-3-hydroxybutanoate Chemical compound COC(=O)CC(O)CCl WMRINGSAVOPXTE-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- JQBCKRZQAMELAD-UHFFFAOYSA-N 1-hydroxypyrrolidin-2-one Chemical compound ON1CCCC1=O JQBCKRZQAMELAD-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- LCHQHZMPERBYFH-UHFFFAOYSA-N 2-bromo-3-hydroxybutanoic acid Chemical compound CC(O)C(Br)C(O)=O LCHQHZMPERBYFH-UHFFFAOYSA-N 0.000 description 1
- AKDAXGMVRMXFOO-UHFFFAOYSA-N 4-chloro-3-hydroxybutanoic acid Chemical compound ClCC(O)CC(O)=O AKDAXGMVRMXFOO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- AIZRKZQHJNWBEI-UHFFFAOYSA-N ethyl 4-bromo-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)CBr AIZRKZQHJNWBEI-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、■−ベンジルー４−ヒドロキシー２−ピロリ
ジノン及びその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to -benzyl-4-hydroxy-2-pyrrolidinone and a method for producing the same.
本化合物は医薬、農薬合成中間体、各種薬品合成中間体
として多様な用途が期待される有用な化合物である。例
えば本化合物を還元して得られる１−ベンジル−３−ピ
ロリジノールは有用な医薬品中間体である。This compound is a useful compound that is expected to have a variety of uses as a pharmaceutical, an intermediate for the synthesis of agricultural chemicals, and an intermediate for the synthesis of various drugs. For example, 1-benzyl-3-pyrrolidinol obtained by reducing this compound is a useful pharmaceutical intermediate.
（従来の技術）
本発明の１−ベンジル−４−ヒドロキシ−２−ピロリジ
ノンは現在までに合成された例のない新規化合物である
。従って、その製造法に関する従来の知見はない。(Prior Art) 1-Benzyl-4-hydroxy-2-pyrrolidinone of the present invention is a novel compound that has never been synthesized to date. Therefore, there is no conventional knowledge regarding its manufacturing method.
（課題を解決するための手段）
本発明は、４−ハロ−３−ヒドロキシ酪酸エステルにベ
ンジルアミンあるいはその塩またはそれらの混合物を反
応させることを特徴とする新規化合物１−ベンジル−４
−ヒドロキシ−２−ピロリジノンの製造法に関する。本
発明の方法は容易に合成し得る安価な原料と安価な触媒
を使用して実施でき、３工程の反応を中間体を単離する
ことなく１工程で行える画期的な方法であり、操作も簡
単である。すなわち４−ハロ−３−ヒドロキシ酪酸エス
テルとベンジルアミンあるいはその塩あるいはそれらの
混合物とを溶媒に溶解し、塩基の存在下、加熱反応させ
るだけで目的とする１−ベンジル−４−ヒドロキシ−２
−ピロリジノンを良好な収率で得ることができる。(Means for Solving the Problems) The present invention provides a novel compound 1-benzyl-4 characterized by reacting 4-halo-3-hydroxybutyric acid ester with benzylamine, a salt thereof, or a mixture thereof.
-Relating to a method for producing hydroxy-2-pyrrolidinone. The method of the present invention can be carried out using inexpensive raw materials and catalysts that can be easily synthesized, and is an innovative method that can perform a three-step reaction in one step without isolating intermediates. is also easy. That is, the desired 1-benzyl-4-hydroxy-2 can be obtained by simply dissolving 4-halo-3-hydroxybutyric acid ester and benzylamine or a salt thereof, or a mixture thereof in a solvent and reacting with heating in the presence of a base.
- Pyrrolidinone can be obtained in good yield.
合成原料として４−ハロアセト酢酸エステルの還元によ
り容易に合成される４−ハロ−３−ヒドロキシ酪酸エス
テル、たとえば４−クロロ−３−ヒドロキシ酪酸メチル
、４−クロロ−３−ヒドロキシ酪酸エチル、４−ブロモ
−３−ヒドロキシ酪酸メチル、４−ブロモ−３−ヒドロ
キシ酪酸エチルと、遊離のベンジルアミンあるいはその
無機酸塩、たとえば塩酸塩、硫酸塩、あるいはその有機
酸塩、たとえば酢酸塩、酪酸塩、メタンスルホン酸塩、
ｐ−トルエンスルホン酸塩、あるいはそれらの混合物を
用いることができる。4-halo-3-hydroxybutyrate easily synthesized by reduction of 4-haloacetoacetate as a synthetic raw material, such as methyl 4-chloro-3-hydroxybutyrate, ethyl 4-chloro-3-hydroxybutyrate, 4-bromo - Methyl 3-hydroxybutyrate, ethyl 4-bromo-3-hydroxybutyrate and free benzylamine or its inorganic acid salts, such as hydrochloride, sulfate, or its organic acid salts, such as acetate, butyrate, methanesulfone. acid salt,
p-Toluenesulfonate or a mixture thereof can be used.
本発明の方法を実施するには、アルコール系、エーテル
系、有機ハロゲン系、芳香族系、エステル系の溶媒のい
ずれか、ならびにこれらの混合溶媒を用いるか、あるい
は無溶媒系で反応すればよいが、メタノール、エタノー
ル、プロパツール、イソプロパツールなどのアルコール
系溶媒を用いるのが望ましい。本反応の速度、収率を向
上させるためには、０．５〜２当量の塩基を添加すると
よく、使用できる無機塩基として、たとえば炭酸ナトリ
ウム、炭酸カリウム、炭酸リチウム、アンモニアなどが
用いられ、有機塩基として、たとえばトリメチルアミン
、トリエチルアミン、ピリジン、ピペリジン、ピペラジ
ンなどを用いることができるが、望ましくは炭酸ナトリ
ウムを用いる。反応温度は２０〜１８０°Ｃの範囲で実
施できるが、６０〜１２０’Ｃで行なうとよい。反応時
間は通常１時間〜３日であり、反応条件により異なる。To carry out the method of the present invention, any one of alcohol-based, ether-based, organic halogen-based, aromatic, and ester-based solvents, or a mixed solvent thereof may be used, or the reaction may be carried out without a solvent. However, it is preferable to use an alcoholic solvent such as methanol, ethanol, propatool, isopropateol, or the like. In order to improve the rate and yield of this reaction, it is recommended to add 0.5 to 2 equivalents of a base. Examples of inorganic bases that can be used include sodium carbonate, potassium carbonate, lithium carbonate, ammonia, etc. As the base, for example, trimethylamine, triethylamine, pyridine, piperidine, piperazine, etc. can be used, but sodium carbonate is preferably used. The reaction temperature can range from 20 to 180°C, but preferably from 60 to 120°C. The reaction time is usually 1 hour to 3 days and varies depending on the reaction conditions.
反応終了後、反応液を濾過し、得られたＦ液を濃縮する
ことにより容易に目的生成物の粗オイルを取得すること
ができる。精製はシリカゲルカラムクロマトグラフィー
、溶剤からの結晶化、蒸留などで行なえばよい。After the reaction is completed, the crude oil of the desired product can be easily obtained by filtering the reaction solution and concentrating the obtained liquid F. Purification may be performed by silica gel column chromatography, crystallization from a solvent, distillation, etc.
（実施例）
つぎに実施例をあげて本発明をさらに詳しく説明するが
、本発明はかかる実施例のみに限定されるものではない
。(Examples) Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
４−クロロ−３−ヒドロキシ酪酸エチル（１，６７，９
，ＩＯミリモル）および、ベンジルアミン（１，０７ｙ
１ ｔｏ＜リモル）をエタノールＬＯａ＋ｌに溶解し、
炭酸ナトリウム（０，５３ｇ、５ミリモル）を加え、５
０時間還流した。反応後、濾過して塩を除き、Ｆ液を濃
縮し、粗生成物のオイル１．８０ｇを得た。Example 1 Ethyl 4-chloro-3-hydroxybutyrate (1,67,9
, IO mmol) and benzylamine (1,07y
1 to < mol) in ethanol LOa+l,
Add sodium carbonate (0.53 g, 5 mmol) and
It was refluxed for 0 hours. After the reaction, the salt was removed by filtration, and the F solution was concentrated to obtain 1.80 g of crude product oil.
このオイルをシリカゲルカラムクロマトグラフィー（展
開溶媒：酢酸エチル）により精製し、ｌ−ベンジル−４
−ヒドロキシ−２−ピロリジノンの結晶１．２１ｇを得
た。収率６３％。ｍｐ７７〜７９℃Ｏ
死票分析（Ｃ１ｌ ＨＩ３０２ Ｎとして）計算値（％
）Ｃ６９，０９、Ｈ６，８５、Ｎ ７．３２測定値（
％）Ｃ６９，１２、Ｈ６，８５、Ｎ ７．３０ＩＨ−
ＮＭＴｔ（９０ＭＨｚＳ ＣＤＣｌ ａ ） δｐｐｍ
：２．２２−２．７５ （２Ｈ）、３．０５−８．５
０ （２Ｈ）、３．９０（ＩＨ）、４．１８−４．５８
（ＩＨ）、４．３５（２Ｈ） 、７．１８（５Ｈ）
ＫＢｒ −１
ｖ ｃｍ ３８００、１６７０、１２
９０．７４０ａＸ
実施例２
４−クロロ−３−ヒドロキシ酪酸メチル（１，５３塩（
１，４４ｇ、１０ミリモル）をメタノール１０ｍ１に溶
解し、炭酸ナトリウム（１，０６１１１０Ｅリモル）を
加え６０時間還流した。実施例１と同様に後処理を行な
った後、酢酸エチル：ヘキサンより結晶化を行ない、■
−ベンジルー４−ヒドロキシー２−ピロリジノン０．９
８ｇを得た。収率５１％。This oil was purified by silica gel column chromatography (developing solvent: ethyl acetate), and l-benzyl-4
1.21 g of crystals of -hydroxy-2-pyrrolidinone were obtained. Yield 63%. mp77-79℃O Death chart analysis (as C1l HI302 N) Calculated value (%
) C69,09, H6,85, N 7.32 measured value (
%) C69,12, H6,85, N 7.30IH-
NMTt(90MHzS CDCla) δppm
:2.22-2.75 (2H), 3.05-8.5
0 (2H), 3.90 (IH), 4.18-4.58
(IH), 4.35 (2H), 7.18 (5H) KBr -1 v cm 3800, 1670, 12
90.740aX Example 2 Methyl 4-chloro-3-hydroxybutyrate (1,53 salt (
1,44 g, 10 mmol) was dissolved in 10 ml of methanol, sodium carbonate (1,061,110 E mol) was added, and the mixture was refluxed for 60 hours. After post-treatment in the same manner as in Example 1, crystallization was performed from ethyl acetate:hexane, and
-Benzy-4-hydroxy-2-pyrrolidinone 0.9
8g was obtained. Yield 51%.
実施例３
４−クロロ−３−ヒドロキシ酪酸エチルのかわりに４−
ブロモ−３−ヒドロキシ酪酸エチル（２，１１ソ、１０
ミリモル）を用いて実施例１と同様に反応を行ない、１
−ベンジル−４−ヒドロキシ−２−ピロリジノン０．８
２ｇを得た。収率４３％０実施例４
４−クロロ−３−ヒドロキシ酪酸メチルのかわりに４−
ブロモ−３−ヒドロキシ酪酸メチル（１，９７９、ＩＯ
Ｅリモル）を用いて実施例１と同様に反応を行ない、１
−ベンジル−４−ヒドロキシ−２−ピロリジノン０．９
１ｇを得た。収率４８％。Example 3 4-chloro-3-hydroxybutyrate ethyl
Ethyl bromo-3-hydroxybutyrate (2,11 so, 10
The reaction was carried out in the same manner as in Example 1 using 1 mmol).
-Benzyl-4-hydroxy-2-pyrrolidinone 0.8
2g was obtained. Yield 43%0 Example 4 4-chloro-3-hydroxybutyrate methyl 4-
Methyl bromo-3-hydroxybutyrate (1,979, IO
A reaction was carried out in the same manner as in Example 1 using 1
-Benzyl-4-hydroxy-2-pyrrolidinone 0.9
1g was obtained. Yield 48%.
Claims (2)
ジノン。(1) 1-benzyl-4-hydroxy-2-pyrrolidinone represented by the formula ▲Mathematical formulas, chemical formulas, tables, etc.▼.
ルアミンあるいはその塩またはそれらの混合物を反応さ
せることを特徴とする１−ベンジル−４−ヒドロキシ−
２−ピロリジノンの製造法。(2) 1-benzyl-4-hydroxy-, which is characterized by reacting 4-halo-3-hydroxybutyric acid ester with benzylamine, a salt thereof, or a mixture thereof.
Method for producing 2-pyrrolidinone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8363088A JPH01254658A (en) | 1988-04-04 | 1988-04-04 | Novel pyrrolidinone and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8363088A JPH01254658A (en) | 1988-04-04 | 1988-04-04 | Novel pyrrolidinone and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01254658A true JPH01254658A (en) | 1989-10-11 |
Family
ID=13807788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8363088A Pending JPH01254658A (en) | 1988-04-04 | 1988-04-04 | Novel pyrrolidinone and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01254658A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000015610A1 (en) * | 1998-09-17 | 2000-03-23 | Samsung Fine Chemicals Co., Ltd. | The preparation of n-substituted-hydroxycycloalkylamine derivatives |
| KR100711938B1 (en) * | 2005-08-29 | 2007-05-02 | 한국화학연구원 | Method for preparing stereoselective 4-hydroxy-2-pyrrolidinone |
-
1988
- 1988-04-04 JP JP8363088A patent/JPH01254658A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000015610A1 (en) * | 1998-09-17 | 2000-03-23 | Samsung Fine Chemicals Co., Ltd. | The preparation of n-substituted-hydroxycycloalkylamine derivatives |
| KR100711938B1 (en) * | 2005-08-29 | 2007-05-02 | 한국화학연구원 | Method for preparing stereoselective 4-hydroxy-2-pyrrolidinone |
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