JPH0582371B2 - - Google Patents
Info
- Publication number
- JPH0582371B2 JPH0582371B2 JP59140964A JP14096484A JPH0582371B2 JP H0582371 B2 JPH0582371 B2 JP H0582371B2 JP 59140964 A JP59140964 A JP 59140964A JP 14096484 A JP14096484 A JP 14096484A JP H0582371 B2 JPH0582371 B2 JP H0582371B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl group
- formula
- lower alkyl
- optically active
- 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 - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 20
- 150000001414 amino alcohols Chemical class 0.000 claims description 15
- 229910000085 borane Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 ketone compounds Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- GEJJWYZZKKKSEV-UHFFFAOYSA-N 2-amino-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(N)C(O)C1=CC=CC=C1 GEJJWYZZKKKSEV-UHFFFAOYSA-N 0.000 description 1
- GPEZBPIDADAHQT-UHFFFAOYSA-N 2-amino-1-(2,4,6-trimethylphenyl)propan-1-ol Chemical compound CC(N)C(O)C1=C(C)C=C(C)C=C1C GPEZBPIDADAHQT-UHFFFAOYSA-N 0.000 description 1
- ZWYOPUOIHUHDFO-UHFFFAOYSA-N 2-amino-1-(2,4-dimethoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(C(O)C(C)N)C(OC)=C1 ZWYOPUOIHUHDFO-UHFFFAOYSA-N 0.000 description 1
- FHGCXNHXFVLMBN-UHFFFAOYSA-N 2-amino-1-(2,4-dimethylphenyl)propan-1-ol Chemical compound CC(N)C(O)C1=CC=C(C)C=C1C FHGCXNHXFVLMBN-UHFFFAOYSA-N 0.000 description 1
- BGSGDJXRVUYFFR-UHFFFAOYSA-N 2-amino-1-(2,5-diethoxyphenyl)propan-1-ol Chemical compound CCOC1=CC=C(OCC)C(C(O)C(C)N)=C1 BGSGDJXRVUYFFR-UHFFFAOYSA-N 0.000 description 1
- LAZIJOOPOWFIQW-UHFFFAOYSA-N 2-amino-1-(2,5-diethoxyphenyl)propan-1-ol;hydrochloride Chemical compound Cl.CCOC1=CC=C(OCC)C(C(O)C(C)N)=C1 LAZIJOOPOWFIQW-UHFFFAOYSA-N 0.000 description 1
- PDGKXNKYNSNSSF-UHFFFAOYSA-N 2-amino-1-(2,5-dimethylphenyl)propan-1-ol Chemical compound CC(N)C(O)C1=CC(C)=CC=C1C PDGKXNKYNSNSSF-UHFFFAOYSA-N 0.000 description 1
- YELZOEGABBRADC-UHFFFAOYSA-N 2-amino-1-(2,5-dimethylphenyl)propan-1-ol;hydrochloride Chemical compound Cl.CC(N)C(O)C1=CC(C)=CC=C1C YELZOEGABBRADC-UHFFFAOYSA-N 0.000 description 1
- YTITXUIVBVJQSM-UHFFFAOYSA-N 2-amino-1-(2,5-dipropoxyphenyl)propan-1-ol Chemical compound CCCOC1=CC=C(OCCC)C(C(O)C(C)N)=C1 YTITXUIVBVJQSM-UHFFFAOYSA-N 0.000 description 1
- YDKIHLWHZQPQKA-UHFFFAOYSA-N 2-amino-1-(2-ethoxy-5-methylphenyl)propan-1-ol Chemical compound CCOC1=CC=C(C)C=C1C(O)C(C)N YDKIHLWHZQPQKA-UHFFFAOYSA-N 0.000 description 1
- KWDGMSAUEPVGNP-UHFFFAOYSA-N 2-amino-1-(2-ethoxyphenyl)propan-1-ol Chemical compound CCOC1=CC=CC=C1C(O)C(C)N KWDGMSAUEPVGNP-UHFFFAOYSA-N 0.000 description 1
- MZIWHUAXHNXOPQ-UHFFFAOYSA-N 2-amino-1-(2-ethoxyphenyl)propan-1-ol;hydrochloride Chemical compound Cl.CCOC1=CC=CC=C1C(O)C(C)N MZIWHUAXHNXOPQ-UHFFFAOYSA-N 0.000 description 1
- TZOQRNSNVWMTCO-UHFFFAOYSA-N 2-amino-1-(2-methoxy-5-methylphenyl)propan-1-ol Chemical compound COC1=CC=C(C)C=C1C(O)C(C)N TZOQRNSNVWMTCO-UHFFFAOYSA-N 0.000 description 1
- MSXYXOAJXBSUPP-UHFFFAOYSA-N 2-amino-1-(2-methoxyphenyl)propan-1-ol Chemical compound COC1=CC=CC=C1C(O)C(C)N MSXYXOAJXBSUPP-UHFFFAOYSA-N 0.000 description 1
- MQALEGRDYROFAZ-UHFFFAOYSA-N 2-amino-1-(2-phenylmethoxyphenyl)propan-1-ol Chemical compound CC(N)C(O)C1=CC=CC=C1OCC1=CC=CC=C1 MQALEGRDYROFAZ-UHFFFAOYSA-N 0.000 description 1
- JGCAGWRCIWJRQN-UHFFFAOYSA-N 2-amino-1-(2-propoxyphenyl)propan-1-ol Chemical compound CCCOC1=CC=CC=C1C(O)C(C)N JGCAGWRCIWJRQN-UHFFFAOYSA-N 0.000 description 1
- HYUUFMZECRUBNL-UHFFFAOYSA-N 2-amino-1-(4-methoxy-2-methylphenyl)propan-1-ol Chemical compound COC1=CC=C(C(O)C(C)N)C(C)=C1 HYUUFMZECRUBNL-UHFFFAOYSA-N 0.000 description 1
- DRRDLGZGYCBXDX-UHFFFAOYSA-N 2-amino-1-(5-chloro-2-methoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(Cl)C=C1C(O)C(C)N DRRDLGZGYCBXDX-UHFFFAOYSA-N 0.000 description 1
- JPXHVMVICUNHJZ-UHFFFAOYSA-N 2-amino-1-naphthalen-1-ylpropan-1-ol Chemical compound C1=CC=C2C(C(O)C(N)C)=CC=CC2=C1 JPXHVMVICUNHJZ-UHFFFAOYSA-N 0.000 description 1
- RTTMUDAKUKBUBR-UHFFFAOYSA-N 2-amino-1-naphthalen-1-ylpropan-1-ol;hydrochloride Chemical compound Cl.C1=CC=C2C(C(O)C(N)C)=CC=CC2=C1 RTTMUDAKUKBUBR-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- WJAJPNHVVFWKKL-UHFFFAOYSA-N Methoxamine Chemical compound COC1=CC=C(OC)C(C(O)C(C)N)=C1 WJAJPNHVVFWKKL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RMIGTEGRHJUHHM-UHFFFAOYSA-N propan-1-ol;hydrochloride Chemical compound Cl.CCCO RMIGTEGRHJUHHM-UHFFFAOYSA-N 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14096484A JPS6122091A (ja) | 1984-07-06 | 1984-07-06 | 水素化ホウ素系還元剤およびその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14096484A JPS6122091A (ja) | 1984-07-06 | 1984-07-06 | 水素化ホウ素系還元剤およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6122091A JPS6122091A (ja) | 1986-01-30 |
| JPH0582371B2 true JPH0582371B2 (es) | 1993-11-18 |
Family
ID=15280912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14096484A Granted JPS6122091A (ja) | 1984-07-06 | 1984-07-06 | 水素化ホウ素系還元剤およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6122091A (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3779456T2 (de) * | 1986-03-14 | 1993-01-07 | Sumitomo Chemical Co | Verfahren zur herstellung von optisch aktiven aminen. |
| EP0846107A1 (en) * | 1995-06-06 | 1998-06-10 | Pharmeco Laboratories, Inc. | Stereoselective method for synthesizing dolaphenine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5946234A (ja) * | 1982-09-09 | 1984-03-15 | Kyowa Hakko Kogyo Co Ltd | 光学活性アルコ−ルの製造方法 |
| JPH051273A (ja) * | 1991-06-26 | 1993-01-08 | Inoac Corp | 二成分系ポリウレタン発泡シーリング材組成物 |
-
1984
- 1984-07-06 JP JP14096484A patent/JPS6122091A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5946234A (ja) * | 1982-09-09 | 1984-03-15 | Kyowa Hakko Kogyo Co Ltd | 光学活性アルコ−ルの製造方法 |
| JPH051273A (ja) * | 1991-06-26 | 1993-01-08 | Inoac Corp | 二成分系ポリウレタン発泡シーリング材組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6122091A (ja) | 1986-01-30 |
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