Vinyl isobutyl ether → HCID 54165959, Verbindung

HRID 428320

Reaktionsgleichung

Reaktionsgleichung von HRID 428320
[CH:1]([N:4]([CH:29]([CH3:31])[CH3:30])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:39]([O:43]C=C)[CH:40](C)C.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:1]([N:4]([CH:29]([CH3:31])[CH3:30])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18]([C:39](=[O:43])[CH3:40])[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 7992Vinyl isobutyl etherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

Produkt 1

HCID 54165959HCID 54165959, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of (R)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropanamine (Example 12) (10.2 g, 21.23 mmol) in DMF (100 mL) under nitrogen atmosphere at room temperature were sequentially added triethylamine (2.58 g, 25.47 mmol), TlOAc (6.15 g, 23.35 mmol), isobutylvinylether (14 mL, 106.14 mmol), DPPP (0.87 g, 2.12 mmol) and Pd(OAc)2 (0.24 g, 1.06 mmol). The reaction temperature was raised to 100° C. and stirred for 3 hours, cooled to room temperature, filtered and treated with HCl (5%, 250 mL) and stirred for another 2 hours. The reaction mixture was repeatedly extracted with dichloromethane and the combined organic layers were dried (MgSO4), filtered and the solvent evaporated. Triethylamine and DMF were destined off under reduced pressure to yield 9 g (98%); 1H NMR (CDCl3) δ1.22 (m, 12H), 2.52-2.70 (m, 7H), 3.40 (br, 2H), 4.34 (t, 1H), 5.10 (s, 1H), 6.90 (d, 1H), 7.17-7.40 (m, 10H), 7.82 (m, 1H) and 7.92 (s, 1H).

Aufarbeitung

  1. customat room temperature
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. additiontreated with HCl (5%, 250 mL)
  5. stirringstirred for another 2 hours
  6. extractionThe reaction mixture was repeatedly extracted with dichloromethane
  7. dry with materialthe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customto yield 9 g (98%)

Quellen und Nachweise

ORD-Eintrag
ord-1c4499c960ae4932a4e9ac8d078bc00c
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313132B1

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