HCID 66832833, Verbindung → HCID 66833605, Verbindung

HRID 579505

Reaktionsgleichung

Reaktionsgleichung von HRID 579505
[BH3:1].[OH:2][C:3]([C:6]([OH:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:10]([C:14]1([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[N:15]1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:11][CH:12]=[CH2:13]>ClCCl.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir].C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:19][C:16]1([CH3:20])[N:15]([C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[C:14]([CH2:10][CH2:11][CH2:12][CH2:13][B:1]2[O:9][C:6]([CH3:8])([CH3:7])[C:3]([CH3:5])([CH3:4])[O:2]2)([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:18][O:17]1

Komponenten

6

Edukt 2

HCID 66832833HCID 66832833, VerbindungHCID 178419189HCID 178419189, Verbindung

Produkt 1

HCID 66833605HCID 66833605, VerbindungAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 742671,2-Bis(diphenylphosphino)ethaneKatalysatorHCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

While under an argon atmosphere, a solution of chloro(1,5-cyclooctadiene) iridium(I) dimer (15 mg, 0.022 mmol) and 1,2-bis(diphenyl-phosphino) ethane (18 mg, 0.044 mmol) in dichloromethane (5 mL) was treated with pinacol borane (225 mg, 1.76 mmol, 0.26 mL) and stirred for 15 minutes. To this mixture was added a solution of 3-benzyl 4-ethyl 4-(but-3-enyl)-2,2-dimethyloxazolidine-3,4-dicarboxylate (530 mg, 1.47 mmol) in dichloromethane (5 mL). After stirring for 19 h at room temperature the solution was concentrated and purified using a combiflash system (24 g column, eluting with 5-50% (ethyl acetate in heptanes) to give 3-benzyl 4-ethyl 2,2-dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)oxazolidine-3,4-dicarboxylate (470 mg, 65%). 1H NMR (CDCl3) δ: 7.22 (m, 5H), 5.01 (m, 2H), 3.91 (m, 4H), 2.20-2.01 (m, 1H), 1.75 (m, 1H), 1.51 (2s, 6H), 1.29 (m, 4H), 1.16 (s, 12H), 1.02 (t, J=7.2 Hz, 3H), 0.69 (t, 2H). MS found for C26H40BNO7 m/z [490 (M+1), 522 (M+Na)].

Aufarbeitung

  1. stirringAfter stirring for 19 h at room temperature the solution
  2. concentrationwas concentrated
  3. custompurified
  4. washeluting with 5-50% (ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-e47af45f283f4e74866134f98b723080
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

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