JP2010508240A - (1r,2r)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノールの製造方法 - Google Patents
(1r,2r)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノールの製造方法 Download PDFInfo
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- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
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- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
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- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
- C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
- C07C225/08—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
- C07C225/10—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings with doubly-bound oxygen atoms bound to carbon atoms not being part of rings
Abstract
Description
を、グリニャール条件下、不活性反応媒体中で、エチルマグネシウムハライドと反応させる工程を含む、(1R,2R)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノールまたはその酸付加塩の製造方法を提供することによって満たされる。
を、グリニャール条件下、不活性反応媒体中で、エチルマグネシウムハライドと反応させる工程、
(b)得られた一般式(II)の化合物
を、一般式(III)の化合物
に、場合により酸付加塩の形で、変換する工程、
(c)得られた一般式(III)の化合物を脱保護して、式(IV)の(1R,2R)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノール
(d)場合により、得られた(1R,2R)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノールを、酸付加塩に転化する工程
を含む、(1R,2R)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノールまたはその酸付加塩の製造方法である。
反応式1
を、マンニッヒ条件下、不活性反応媒体中で、ジメチルアミン塩酸塩およびパラホルムアルデヒドと反応させ、
(a’’)次に、得られた一般式(VI)の化合物
を分割すること
によって得ることができる。
を、不活性反応媒体中、水素の存在下で、適切な触媒を使って水素化することによって行われる。
電気式羽根撹拌機、ガス導入ライン、Pt100温度測定装置および油ベースの冷却/加熱システムを装備した100L(L=リットル)二重ジャケット容器中で、1−(3−メトキシフェニル)プロパン−1−オン(16.42kg、100mol)、ジメチルアミン塩酸塩(8.97kg、110mol)、パラホルムアルデヒド(3.30kg、110mol)および塩酸水溶液(32重量%、1.14kg)を、窒素雰囲気下のエタノールに溶解した。反応混合物を16時間還流し、3.5時間以内に25℃まで冷却し、その温度で1時間撹拌した。その懸濁液を遠心分離器で分離し、各7Lのアセトンで3回洗浄した。3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オン塩酸塩を水(12.5L)およびtert−ブチル−メチル−エーテル(8.5L)に溶解し、室温で撹拌した。水酸化ナトリウム水溶液(32重量%)を、pH値が10.0〜10.5に達するまで加え、相を分離させた。有機相を減圧下、40℃の温度で、圧力が5mbarに達するまで留去した。3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オンを淡黄色油状物(20.75kg、94%)として得て、それを、これ以上精製せずに次の工程に使用した。
機械式撹拌機、温度測定装置および油浴を装備した2L反応プラント中で、(2R,3R)−O,O’−ジベンゾイル酒石酸一水和物(189.1g、0.5mol)をアセトン(550mL)に溶解し、3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オン(110.6g、0.5mol)を加えた。反応混合物を35℃〜40℃に27時間加熱し、25℃まで冷ました。その懸濁液を吸い上げて(siphoned off)、(S)−3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オン(2R,3R)−O,O’−ジベンゾイル酒石酸塩を無色の固体として得た(233.2g、80.5%、ee 96.9%、ee=エナンチオマー過剰率)。
電気式羽根撹拌機、ガス導入ライン、Pt100温度測定装置および油ベースの冷却/加熱システムを装備した10L二重ジャケット容器中で、(2R,3R)−O,O’−ジベンゾイル酒石酸一水和物(2.1kg、5.5mol)をメタノール(555mL)およびアセトン(3340mL)の混合物に溶解し、3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オン(1.23kg、5.56mol)を加えた。反応混合物を35℃〜40℃に24時間加熱し、25℃まで冷ました。その懸濁液を吸い上げて、(S)−3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オン(2R,3R)−O,O’−ジベンゾイル酒石酸塩を無色の固体として得た(2.38kg、74%、ee 98.4%)。
電気式羽根撹拌機、ガス導入ライン、Pt100温度測定装置および油ベースの冷却/加熱システムを装備した10L二重ジャケット容器中で、(S)−3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オン(2R,3R)−O,O’−ジベンゾイル酒石酸塩(968g、1.67mmol、ee 98%)をtert−ブチルメチルエーテル(6L)に懸濁し、ジエチルアミン(384g、5.25mol)を加えた。反応混合物を20℃〜25℃で90分間撹拌し、固体を吸い上げた。濾液を減圧下、40℃の温度で、圧力が4mbarに達するまで濃縮した。(S)−3−(ジメチルアミノ)−1−(3−メトキシフェニル)−2−メチルプロパン−1−オンを無色の油状物として得た(356.7g、96.5%、ee 98%)。
Claims (23)
- (a)一般式(I)
で表わされる化合物を、グリニャール条件下、不活性反応媒体中で、エチルマグネシウムハライドと反応させる工程、
(b)得られた一般式(II)
で表わされる化合物を、一般式(III)
で表わされる化合物に、場合により酸付加塩の形で、変換する工程、
(c)得られた一般式(III)の化合物を脱保護して、式(IV)
(d)場合により、得られた(1R,2R)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノールを、酸付加塩に転化する工程
を含む、(1R,2R)−3−(3−ジメチルアミノ−1−エチル−2−メチル−プロピル)−フェノールまたはその酸付加塩の製造方法。 - Rがメチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチル、n−ペンチル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、ベンジル、フェネチル、テトラヒドロピラニル、−C(=O)−CH3、−C(=O)−C2H5、−C(=O)−CH(CH3)2または−C(=O)−C(CH3)3を表す、請求項1記載の方法。
- Rがメチル、エチル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、ベンジル、フェネチル、テトラヒドロピラニルまたは−C(=O)−CH3を表す、請求項1または2記載の方法。
- Rがメチル、ベンジルまたはテトラヒドロピラニルを表す、請求項1〜3のいずれか1つに記載の方法。
- 工程(a)で使用されるエチルマグネシウムハライドがクロリドまたはブロミドである、請求項1〜4のいずれか1つに記載の方法。
- 不活性反応媒体がジエチルエーテル、テトラヒドロフラン、2−メチルテトラヒドロフラン、tert−ブチル−メチルエーテル、ジイソプロピルエーテルまたはその任意の混合物より成る群から選ばれる、請求項1〜5のいずれか1つに記載の方法。
- Rがメチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチル、n−ペンチル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、ベンジル、フェネチル、テトラヒドロピラニル、−C(=O)−CH3、−C(=O)−C2H5、−C(=O)−CH(CH3)2または−C(=O)−C(CH3)3を表す、請求項7に記載の方法。
- Rがメチル、エチル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、ベンジル、フェネチル、テトラヒドロピラニルまたは−C(=O)−CH3を表す、請求項7または8記載の方法。
- Rがメチル、ベンジルまたはテトラヒドロピラニルを表す、請求項7〜9のいずれか1つに記載の方法。
- 工程(a’’)における分割が、一般式(VI)の化合物をL−(−)−ジベンゾイル酒石酸、L−(−)−ジベンゾイル酒石酸・H2OおよびD−(−)−酒石酸からなる群より選択されるキラル酸と反応させた後、得られた塩を分離し、対応する式(I)の化合物を遊離塩基の形で遊離させることによって行われる、請求項7〜10のいずれか1つに記載の方法。
- 分割が、メタノール、エタノール、1−プロパノール、2−プロパノールおよびその任意の混合物より成る群から選ばれるアルコール系反応媒体中で行われる、請求項11記載の方法。
- Rがメチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチル、n−ペンチル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、ベンジル、フェネチル、テトラヒドロピラニル、−C(=O)−CH3、−C(=O)−C2H5、−C(=O)−CH(CH3)2または−C(=O)−C(CH3)3を表す、請求項13記載の方法。
- Rがメチル、エチル、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、ベンジル、フェネチル、テトラヒドロピラニルまたは−C(=O)−CH3を表す、請求項13または14記載の方法。
- Rがメチル、ベンジルまたはテトラヒドロピラニルを表す、請求項13〜15のいずれか1つに記載の方法。
- 脱水工程(b’)後に、工程(b’’)における水素化が均一触媒作用によって達成される、請求項13〜16のいずれか1つに記載の方法。
- 脱水工程(b’)が酸によって触媒される、請求項13〜17のいずれか1つに記載の方法。
- 酸がギ酸、塩酸、硫酸、メタンスルホン酸、臭化水素酸またはその任意の混合物より成る群から選ばれる、請求項18記載の方法。
- 工程(b’’)の水素化が不均一触媒作用によって達成される、請求項13〜16のいずれか1つに記載の方法。
- 水素化に使用される触媒がラネーニッケル、パラジウム、パラジウム担持炭素、白金、白金担持炭素、ルテニウム担持炭素またはロジウム担持炭素からなる群より選択される、請求項20記載の方法。
- 反応媒体がジエチルエーテル、テトラヒドロフラン、2−メチルテトラヒドロフラン、tert−ブチル−メチルエーテル、ジイソプロピルエーテルまたはその任意の混合物より成る群から選ばれる、請求項13〜21のいずれか1つに記載の方法。
- 工程b)がHによるOH基の直接置換反応であり、好ましくはワンポット反応で行われる、請求項1〜12のいずれか1つに記載の方法。
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EP06015338.4 | 2006-07-24 | ||
EP06015338 | 2006-07-24 | ||
PCT/EP2007/006515 WO2008012047A1 (en) | 2006-07-24 | 2007-07-23 | Process for the preparation of (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
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JP2010508240A true JP2010508240A (ja) | 2010-03-18 |
JP5612308B2 JP5612308B2 (ja) | 2014-10-22 |
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US (7) | US8877974B2 (ja) |
EP (4) | EP3868739B1 (ja) |
JP (1) | JP5612308B2 (ja) |
KR (1) | KR101423996B1 (ja) |
CN (1) | CN101495445B (ja) |
AU (1) | AU2007278464C1 (ja) |
BR (1) | BRPI0714558B8 (ja) |
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JP2013512276A (ja) * | 2009-12-01 | 2013-04-11 | ユーティカルズ ソシエタ ペル アチオニ | タペンタドールおよびその中間体を調製するための新しい方法 |
JP2013529676A (ja) * | 2010-07-02 | 2013-07-22 | ユーティカルズ ソシエタ ペル アチオニ | タペンタドールおよびその中間体を合成する新規のプロセス |
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