Triphenylphosphine → (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide

HRID 1865706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865706
[C:1]1([CH2:7][C@H:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[C:1]1([CH2:7][C@H:8]([N:60]=[N+:61]=[N-:62])[C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 11084983(1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanol

Produkt 1

HCID 10955374(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazideAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the method of Itako et al. (Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 48(35), 1992, 7251-7264), a solution of (1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanol (1.3 g, 6.3 mmol, from Reference Example 3) in tetrahydrofuran (60 mL) is cooled to 0° C. (ice-water bath). To the solution is added successively triphenylphosphine (1.8 g, 6.9 mmol), diethylazodicarboxylate (1.1 mL, 6.9 mmol), and diphenylphosphoryl azide (DPPA, 1.6 mL, 6.9 mmol). Following the addition of reagents, the reaction mixture is allowed to warm to room temperature and stir for 47 hours. Following this period, the mixture is concentrated under reduced pressure and purified by flash chromatography (silica gel, hexanes/toluene/diethyl ether) to give 1.2 g of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide as a pale blond oil contaminated with DPPA (detected by 1H NMR).

Aufarbeitung

  1. additionthe addition of reagents
  2. waitFollowing this period
  3. concentrationthe mixture is concentrated under reduced pressure
  4. custompurified by flash chromatography (silica gel, hexanes/toluene/diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-f09f39ff0210452e8621cb6100f4780a
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626023B2

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