Triphenylphosphine → HCID 86708686, Verbindung

HRID 921790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921790
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[OH:27].O[CH:29]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[Cl:15][C:16]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[O:27][CH:33]1[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32]1

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5363146Diisopropyl azodicarboxylateHCID 23288677HCID 23288677, Verbindung

Produkt 1

HCID 86708686HCID 86708686, VerbindungAusbeute 69,2 %

Versuchsvorschrift

DIAD (0.309 mL, 1.495 mmol) was added to a solution of 4-chloro-3-hydroxy-5-nitrobenzonitrile (Example 425B) (223 mg, 1.122 mmol), (+/−)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (200 mg, 1.068 mmol) and triphenylphosphine resin (3 mmol/g loading, 560 mg, 2.136 mmol) in THE (5 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 0-20% ethyl acetate/dichloromethane). (+/−)-tert-butyl 3-(2-chloro-5-cyano-3-nitrophenoxy)pyrrolidine-1-carboxylate (272 mg) was obtained as a yellow solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe crude product was purified by flash chromatography on silica gel using
  4. washan automated ISCO system (40 g column, eluting with 0-20% ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-eb3dd994681847daba10df043af61ed6
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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