Tetramethylammonium fluoride → Tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylate

HRID 1401977

Reaktionsgleichung

Reaktionsgleichung von HRID 1401977
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)(C(C)(C)C)(C)C.[F-].C[N+](C)(C)C>O1CCCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH:16]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:19]2)[CH:11]=1

Komponenten

4

Edukt 2

HCID 67803Tetramethylammonium fluorideHCID 59436503tert-Butyl3-(2-{[tert-butyl(dimethyl)silyl]oxy)-5-chlorophenyl)azetidine-1-carboxylate

Produkt 1

HCID 59436608Tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-Butyl 3-(2-{[tert-butyl(dimethyl)silyl]oxy}-5-chlorophenyl)azetidine-1-carboxylate (Preparation 238, 3.1 g, 7.79 mmol) in tetrahydrofuran (80 ml) was added tetramethylammonium fluoride (1.0 g, 10.74 mmol). The mixture was stirred at room temperature for 18 hours before concentrating in vacuo. The residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution. The organics were dried over sodium sulfate, filtered and evaporated in vacuo to give a reddish brown oil, 2.33 g. This was purified by column chromatography (100 g of silica) eluting with heptane:ethyl acetate (6:4, by volume) to afford the title compound as a reddish brown gum, 850 mg, 38% yield.

Aufarbeitung

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a reddish brown oil, 2.33 g
  7. customThis was purified by column chromatography (100 g of silica)
  8. washeluting with heptane:ethyl acetate (6:4, by volume)

Quellen und Nachweise

ORD-Eintrag
ord-74f3631b0d5d45d783a48016a9097092
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907101B2

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