beta-trimethylsilylethyl (3RS,4RS)-4-(4-fluorophenyl)-3-(4-hydroxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate → (3RS,4RS)-4-(4-fluorophenyl)-3-(4-hydroxy-naphthalen-2-ylmethoxy)-piperidine

HRID 1858561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1858561
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OCC[Si](C)(C)C)=O)[CH2:10][CH:9]2[O:23][CH2:24][C:25]2[CH:34]=[C:33]([OH:35])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[CH:4][CH:3]=1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[O:23][CH2:24][C:25]2[CH:34]=[C:33]([OH:35])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[CH:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 53737733beta-trimethylsilylethyl (3RS,4RS)-4-(4-fluorophenyl)-3-(4-hydroxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Produkt 1

HCID 22126660(3RS,4RS)-4-(4-fluorophenyl)-3-(4-hydroxy-naphthalen-2-ylmethoxy)-piperidineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2724141Tetrabutylammonium FluorideLösungsmittel

Versuchsvorschrift

70 mg (0.141 mmol) of β-trimethylsilylethyl (3RS,4RS)-4-(4-fluorophenyl)-3-(4-hydroxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate were dissolved in 1.0 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) and stirred at room temperature for one hour. Subsequently, the mixture was partitioned between methylene chloride and aqueous 5% sodium hydrogen carbonate solution, then the organic phase was dried over magnesium sulphate and finally the solvent was distilled off under reduced pressure. The crude product (72 mg) was purified by chromatography on silica gel with a 10:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There were obtained 41 mg (83% of theory) of (3RS,4RS)-4-(4-fluorophenyl)-3-(4-hydroxy-naphthalen-2-ylmethoxy)-piperidine as a colourless solid. MS: 352 (M+H)+.

Aufarbeitung

  1. customSubsequently, the mixture was partitioned between methylene chloride and aqueous 5% sodium hydrogen carbonate solution
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. distillationfinally the solvent was distilled off under reduced pressure
  4. customThe crude product (72 mg) was purified by chromatography on silica gel with a 10:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-d8b7c9b75af04502b31423a58c0611d0
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150526

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