Acetic Acid → (3S,4S)-4-[(S)-3-(4-Fluoro-benzyl)-piperidin-1-ylmethyl]-tetrahydro-pyran-3-ylamine

HRID 497493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497493
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([C@@H:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[NH2:21])=O)[CH2:8]2)=[CH:4][CH:3]=1.O1CCCC1.C(O)(=O)C>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][C@@H:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[NH2:21])[CH2:8]2)=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 69748357HCID 69748357, Verbindung

Produkt 1

HCID 21362442(3S,4S)-4-[(S)-3-(4-Fluoro-benzyl)-piperidin-1-ylmethyl]-tetrahydro-pyran-3-ylamineAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

[(S)-3-(4-Fluoro-benzyl)-piperidin-1-yl]-[(3S,4R)-3-aminotetrahydro-pyran-4-yl]-methanone (367 mg, 1.14 mmol) was treated with borane-tetrahydrofuran complex in tetrahydrofuran (1.0 M; 46 mL, 46 mmol) and stirred for 20 h. The mixture was treated slowly with 20% acetic acid in methanol (25 mL), and the resulting mixture was stirred at room temperature for 3 h. The solvents were removed, and the residue was dissolved in water, made basic (pH 11) with 50% sodium hydroxide, and extracted with dichloromethane. The combined organic phases were dried (Na2SO4) and concentrated to provide a gum (313 mg). A portion of this material (175 mg) was purified by flash column chromatography (5% methanol/dichloromethane, containing 0.5% ammonium hydroxide) to provide the product (103 mg, 52%) as an oil which solidified on standing.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 3 h
  2. customThe solvents were removed
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-54e4fb6de3154b5baef64f43a29c6533
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949546B2

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