Ethanolamine → 5-{[4-(2-Azepan-1-yl-ethoxy)-phenyl]-hydroxy-methyl}-6-(2,4,6-trifluoro-phenyl)-naphthalen-2-ol

HRID 1513972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513972
B.C1CN[C@H](C(O)(C2C=CC=CC=2)C2C=CC=CC=2)C1.[N:21]1([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([C:39]3[C:48]4[C:43](=[CH:44][C:45]([OH:49])=[CH:46][CH:47]=4)[CH:42]=[CH:41][C:40]=3[C:50]3[C:55]([F:56])=[CH:54][C:53]([F:57])=[CH:52][C:51]=3[F:58])=[O:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(CN)O>C1COCC1.[Cl-].[Na+].O>[N:21]1([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([CH:37]([OH:38])[C:39]3[C:40]([C:50]4[C:55]([F:56])=[CH:54][C:53]([F:57])=[CH:52][C:51]=4[F:58])=[CH:41][CH:42]=[C:43]4[C:48]=3[CH:47]=[CH:46][C:45]([OH:49])=[CH:44]4)=[CH:33][CH:32]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Komponenten

7

Edukt 4

HCID 700EthanolamineHCID 6331BoraneHCID 27248992-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-HCID 67004267[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[6-hydroxy-2-(2,4,6-trifluoro-phenyl)naphthalen-1-yl]-methanone

Produkt 1

HCID 670049855-{[4-(2-Azepan-1-yl-ethoxy)-phenyl]-hydroxy-methyl}-6-(2,4,6-trifluoro-phenyl)-naphthalen-2-olAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Charge a flask with 1M borane in THF (4 mL) and (R)-(+) α,α-diphenylprolinol (26 mg, 0.1 mmol). Dissolve [4-(2-azepan-1-yl-ethoxy)-phenyl]-[6-hydroxy-2-(2,4,6-trifluoro-phenyl)-naphthalen-1-yl]-methanone (348 mg, 0.7 mmol) in THF (3 mL) and add to the catalyst solution via syringe pump over 1.5 hours at 45° C. Upon completion of the reaction add ethanolamine (0.8 mL, 13.4 mmol) and heat at 45° C. for 2 hours. Cool the reaction to room temperature and add brine (5 mL) and stir for 1 hour. Filter the reaction and separate layers. Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Purify by silica gel chromatography using a 1.5-5% gradient of methanol in dichloromethane to yield 306 mg (88%) of the title compound: mass spectrum (ion spray) m/z=522 (M+H).

Aufarbeitung

  1. temperatureCool
  2. customthe reaction to room temperature
  3. filtrationFilter
  4. customthe reaction
  5. customseparate layers
  6. dry with materialDry the organic layer with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f82e2217949f4c9fb29cb26aec1f8ea0
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217032B2

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