Tetrabutylammonium Fluoride → 3-Hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

HRID 891809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891809
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][CH:19]1[CH2:20][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:29])[N:27]=2)[CH2:22]1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 222428193-t-Butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

Produkt 1

HCID 222429883-Hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidineAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (730 mg, 1.48 mmol) (obtained as described in Reference Example 72(1)) in anhydrous tetrahydrofuran (37 ml) was added a solution of 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (1.78 ml, 1.78 mmol) in an ice bath and the mixture was stirred in an ice bath for 1.5 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (95:5→9:1) as the eluant to afford 3-hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (377 mg, yield 100%) as white crystals.

Aufarbeitung

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-dad8d1a42d67417e9b621675ea235ead
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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