Sodium borohydride → 3-Hydroxy-3-(3-(5-methoxypentylamino)phenyl)propanenitrile

HRID 716770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716770
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=O.[NH2:9][C:10]1[CH:11]=[C:12]([CH:16]([OH:20])[CH2:17][C:18]#[N:19])[CH:13]=[CH:14][CH:15]=1.[BH4-].[Na+]>CO>[OH:20][CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH:11]=1)[CH2:17][C:18]#[N:19]

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 130279335-MethoxypentanalHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

Produkt 1

HCID 672967943-Hydroxy-3-(3-(5-methoxypentylamino)phenyl)propanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-methoxypentanal (0.644 g, 5.54 mmol), 3-(3-aminophenyl)-3-hydroxypropanenitrile (12) (1.0 g, 6.16 mmol) and activated molecular sieves in methanol was stirred at RT for 8 hrs. NaBH4 (0.937 g, 24.6 mmol) was added portion wise to the reaction mixture at 0° C. The reaction mixture was stirred at RT overnight. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. Purification by column chromatography (100-200 silica, 0% to 70% EtOAc—hexanes gradient) gave 3-hydroxy-3-(3-(5-methoxypentylamino)phenyl)propanenitrile as a yellow oil. Yield (0.34 g, 21%); 1H NMR (400 MHz, CDCl3) δ 7.17 (t, J=8.0 Hz, 1H), 6.66 (d, J=7.6 Hz, 1H), 6.62 (s, 1H), 6.56 (d, J=8.0 Hz, 1H), 4.95 (t, J=6.4 Hz, 1H), 3.39 (t, J=6.4 Hz, 2H), 3.33 (s, 3H), 3.12 (t, J=7.2 Hz, 2H), 2.75 (d, J=6.4 Hz, 2H), 1.68-1.59 (m, 4H), 1.51-1.43 (m, 2H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at RT overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customPurification by column chromatography (100-200 silica, 0% to 70% EtOAc—hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d703efb77be747c99c0b4c83df235f2b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193669B2

Notizen zur Reaktion

Wird geladen…