Tetrahydrofuran → HCID 66833480, Verbindung

HRID 579575

Reaktionsgleichung

Reaktionsgleichung von HRID 579575
C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.[CH3:34][C:35]1([CH3:42])[C:39]([CH3:41])([CH3:40])[O:38][BH:37][O:36]1.[C:43]([NH:46][C:47]([C@@H:59]1[CH2:63][CH2:62][N:61]([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([F:71])=[CH:67][CH:66]=2)[CH2:60]1)([CH2:55][CH2:56][CH:57]=[CH2:58])[C:48]([NH:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])(=[O:45])[CH3:44]>C(=O)(O)[O-].[Na+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]>[C:43]([NH:46][C:47]([C@@H:59]1[CH2:63][CH2:62][N:61]([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([F:71])=[CH:67][CH:66]=2)[CH2:60]1)([CH2:55][CH2:56][CH2:57][CH2:58][B:37]1[O:38][C:39]([CH3:41])([CH3:40])[C:35]([CH3:42])([CH3:34])[O:36]1)[C:48]([NH:50][C:51]([CH3:54])([CH3:52])[CH3:53])=[O:49])(=[O:45])[CH3:44]

Komponenten

7

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 742671,2-Bis(diphenylphosphino)ethaneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 66832976HCID 66832976, Verbindung

Produkt 1

HCID 66833480HCID 66833480, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerKatalysatorHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of bis(1,5-cyclooctadiene)diiridium(I) dichloride (35.0 mg, 0.0520 mmol) and 1,2-bis(diphenylphosphino)-ethane (44 mg, 0.11 mmol) in tetrahydrofuran (5 mL, 60 mmol) was cooled to 0° C. After stirring for 10 min 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (120 uL, 0.83 mmol) was added in a single portion via syringe and the reaction mixture was stirred at 0° C. for 5 min before warming to room temperature and stirring an additional 15 min. The reaction mixture was recooled to 0° C. and treated with 2-acetamido-N-tert-butyl-2-[(3R)-1-(4-fluorobenzyl)pyrrolidin-3-yl]hex-5-enamide (210 mg, 0.52 mmol) in tetrahydrofuran (3 mL, 40 mmol) in a single portion. After stirring for 10 min at 0° C., the reaction was warmed to room temperature and stirred an additional 4 h. The mixture was diluted with aqueous sodium bicarbonate, extracted with DCM (3×50 mL), dried over Na2SO4, filtered and concentrated to give 2-acetamido-N-tert-butyl-2-((R)-1-(4-fluorobenzyl)pyrrolidin-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide as a light orange oil that was used without further purification. ESI MS found for C29H47BFN3O4 m/z 532.3 (M+H)+

Aufarbeitung

  1. additionwas added in a single portion via syringe
  2. temperaturebefore warming to room temperature
  3. stirringstirring an additional 15 min
  4. customwas recooled to 0° C.
  5. stirringAfter stirring for 10 min at 0° C.
  6. temperaturethe reaction was warmed to room temperature
  7. stirringstirred an additional 4 h
  8. extractionextracted with DCM (3×50 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-636fe8cc04b74899b11fd1b776eaa443
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

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