Sodium borohydride → 1-Benzyl-3-cyano-4-hydroxypiperidine

HRID 396329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396329
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH:12]([C:17]#[N:18])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]([C:17]#[N:18])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 230037231-Benzyl-4-oxopiperidine-3-carbonitrile

Produkt 1

HCID 230037331-Benzyl-3-cyano-4-hydroxypiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.89 g, 23.37 mmole) was added to the stirred solution of 1-benzyl-3-cyanopiperidin-4-one (2.5 g, 11.68 mmole) in ethanol (125 ml) at 0° C. over a period of 30 min, and stirring was continued for 2 hr at 5° C. The reaction mixture was concentrated to dryness, triturated with water (20 ml) and extracted with ethyl acetate. The extract was concentrated to dryness to furnish 1-benzyl-3-cyano-4-hydroxypiperidine product as oil. Yield 1.85 g (73%) C13H16N2O, m/z 217 (M+1), PMR (CDCl3): 1.78 (2H, m, H5), 2.22 (1H, m, H3), 2.6-3.12 (4H, m, H2 & H6), 3.58 (1H, m, H4), 3.65 (2H, s, CH2—Ar), 7.32 (5H, s, ArH).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water (20 ml)
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f1586bdc0e8f4616bd68a5cc3fe3c191
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608078B2

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