Diethylamine → Chloro[(S)-(-)-2,2 inverted exclamation mark-bis[di(3,5-xylyl)phosphino]-1,1 inverted exclamation mark-binaphthyl][(2S)-(+)-1-(4-methoxyphenyl)-1-(4-methoxyphenyl-kC)-3-methyl-1,2-butanediamine]ruthenium(II)

HRID 1773165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773165
CC1C=CC(C(C)C)=CC=1.[CH3:11][C:12]1[CH:17]=[C:16]([P:18]([C:56]2[CH:61]=[C:60]([CH3:62])[CH:59]=[C:58]([CH3:63])[CH:57]=2)[C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][C:30]=2[P:39]([C:48]2[CH:53]=[C:52]([CH3:54])[CH:51]=[C:50]([CH3:55])[CH:49]=2)[C:40]2[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=2)[CH:15]=[C:14]([CH3:64])[CH:13]=1.[Cl:65][Ru:66]Cl.C(NCC)C.[CH3:73][CH:74]([C@H:76]([NH2:95])[C:77]([NH2:94])([C:86]1[CH:91]=[CH:90][C:89]([O:92][CH3:93])=[CH:88][CH:87]=1)[C:78]1[CH:83]=[CH:82][C:81]([O:84][CH3:85])=[CH:80][CH:79]=1)[CH3:75]>CO>[CH3:63][C:58]1[CH:57]=[C:56]([P:18]([C:16]2[CH:15]=[C:14]([CH3:64])[CH:13]=[C:12]([CH3:11])[CH:17]=2)[C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][C:30]=2[P:39]([C:48]2[CH:49]=[C:50]([CH3:55])[CH:51]=[C:52]([CH3:54])[CH:53]=2)[C:40]2[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=2)[CH:61]=[C:60]([CH3:62])[CH:59]=1.[CH3:75][CH:74]([C@H:76]([NH2:95])[C:77]([NH2:94])([C:78]1[CH:79]=[CH:80][C:81]([O:84][CH3:85])=[CH:82][CH:83]=1)[C:86]1[CH:87]=[CH:88][C:89]([O:92][CH3:93])=[CH:90][CH:91]=1)[CH3:73].[Cl-:65].[Ru+:66]

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 10964285(2S)-1,1-Bis(4-methoxyphenyl)-3-methylbutane-1,2-diamineHCID 72376324chloro[(S)-2,2'-bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II) chloride

Produkt 1

HCID 91972051Chloro[(S)-(-)-2,2 inverted exclamation mark-bis[di(3,5-xylyl)phosphino]-1,1 inverted exclamation mark-binaphthyl][(2S)-(+)-1-(4-methoxyphenyl)-1-(4-methoxyphenyl-kC)-3-methyl-1,2-butanediamine]ruthenium(II)Ausbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Under a nitrogen gas, [RuCl2(p-cymene)]2 3.07 g (5.0 mmol), (S)-XylBINAP 7.35 g (10.0 mmol) and methanol 110 mL were added to a 200 mL 4-neck flask. The mixture was heated to 50° C. and stirred for 2 hours to prepare [RuCl(p-cymene)((S)-xylbinap)]Cl. The reaction solution was cooling down to room temperature, then diethylamine 736 mg (10 mmol) and (S)-DAIPEN 3.48 g (11.1 mmol) were added to the reaction solution, and stirred for 3 hours at 60° C. After concentration, the residue was dissolved in butyl acetate and the precipitated salts were separated by filtration. The filtrate was concentrated and the mixture added with heptane (110 mL) was cooling down to −10° C. The precipitated crystals were filtered to obtain the title compound (11.62 g) with yield of 98%.

Aufarbeitung

  1. temperatureThe reaction solution was cooling down to room temperature
  2. stirringstirred for 3 hours at 60° C
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in butyl acetate
  5. customthe precipitated salts were separated by filtration
  6. concentrationThe filtrate was concentrated
  7. additionthe mixture added with heptane (110 mL)
  8. temperaturewas cooling down to −10° C
  9. filtrationThe precipitated crystals were filtered

Quellen und Nachweise

ORD-Eintrag
ord-d0c7ecaaa869412f8ffd1554d5c7e171
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255049B2

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