Dimethylformamide → HCID 86705548, Verbindung

HRID 2279563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279563
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)(C(O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[N:43]([CH:45]=[O:46])C>CCOC(C)=O>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([N:43]=[C:45]=[O:46])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 68294367HCID 68294367, Verbindung

Produkt 1

HCID 86705548HCID 86705548, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 358 (187 mg, 0.4997 mmol) in DMF (1.5 mL) at RT under nitrogen was added TEA (167.1 μL, 1.199 mmol) neat via syringe followed by DPPA (129.6 μL, 0.5996 mmol) neat by syringe. The solution was stirred for 2 h at RT then warmed to 60° C. After 3 h at 60° C., the reaction was cooled to RT and diluted to 30 mL with EtOAc. The organic extract was washed with H2O (3×30 mL) and brine (1×30 mL). The organics were dried (MgSO4), filtered and concentrated to afford 170 mg (91%) of tert-butyl 4-(3,4-dichlorophenyl)-4-isocyanatopiperidine-1-carboxylate (360) as a clear oil.

Aufarbeitung

  1. temperaturethen warmed to 60° C
  2. waitAfter 3 h at 60° C.
  3. temperaturethe reaction was cooled to RT
  4. extractionThe organic extract
  5. washwas washed with H2O (3×30 mL) and brine (1×30 mL)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8458255fded8411681fa1631e944df46
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133187B2

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