Tetrabutylammonium Fluoride → (9-(3-(1-Fluoro-2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

HRID 471060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471060
[Si]([O:8][CH2:9][CH:10]([C:12]1[CH:13]=[C:14]([CH:37]=[CH:38][CH:39]=1)[CH2:15][N:16]1[CH2:36][CH2:35][C:19]2([O:24][CH2:23][CH2:22][N:21]([C:25]([C:27]3[N:28]=[C:29]([CH:32]([CH3:34])[CH3:33])[S:30][CH:31]=3)=[O:26])[CH2:20]2)[CH2:18][CH2:17]1)[F:11])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:11][CH:10]([C:12]1[CH:13]=[C:14]([CH:37]=[CH:38][CH:39]=1)[CH2:15][N:16]1[CH2:36][CH2:35][C:19]2([O:24][CH2:23][CH2:22][N:21]([C:25]([C:27]3[N:28]=[C:29]([CH:32]([CH3:33])[CH3:34])[S:30][CH:31]=3)=[O:26])[CH2:20]2)[CH2:18][CH2:17]1)[CH2:9][OH:8]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 57989307(9-(3-(2-(tert-Butyldimethylsilyloxy)-1-fluoroethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Produkt 1

HCID 67292595(9-(3-(1-Fluoro-2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (9-(3-(2-(tert-butyldimethylsilyloxy)-1-fluoroethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 39, step e) (0.33 g) in THF (5 mL) was treated with tetrabutylammonium fluoride (1M in THF, 0.69 mL) and stirred at room temperature for 50 minutes. More tetrabutylammonium fluoride (1M in THF, 0.69 mL) was added and the mixture was stirred for a further 80 minutes. The solution was then concentrated onto flash silica and the residue was purified by flash chromatography on silica eluted with 7.5% methanol in dichloromethane to afford the subtitled compound as a white foam. Yield 0.221 g.

Aufarbeitung

  1. stirringthe mixture was stirred for a further 80 minutes
  2. concentrationThe solution was then concentrated onto flash silica
  3. customthe residue was purified by flash chromatography on silica
  4. washeluted with 7.5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-13232a44456442fc8f37cd19895a7613
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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