Benzaldehyde → 3-(3-(Benzylamino)phenyl)-3-hydroxypropanenitrile

HRID 1189974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189974
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:26])[CH2:23][C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:26])[CH2:23][C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

Produkt 1

HCID 672967283-(3-(Benzylamino)phenyl)-3-hydroxypropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

NaBH(OAc)3 (7.84 g, 36.99 mmol) was added to a solution of aniline 12 (2.0 g, 12.33 mmol) and benzaldehyde (1.3 g, 12.33 mmol) in DCM. The resulting mixture was stirred at RT for 5 h and quenched with saturated aqueous NaHCO3. Organic layer was washed with water followed by brine and dried over anhydrous Na2SO4. Organic layer was concentrated under reduced pressure. Purification by flash chromatography (40% to 50% EtOAc—hexanes gradient) gave 3-(3-(benzylamino)phenyl)-3-hydroxypropanenitrile as a pale yellow oil. Yield (2.61 g, 83%); 1H NMR (400 MHz, DMSO-d6) δ 7.36-7.29 (m, 4H), 7.23-7.19 (m, 1H), 6.99 (t, J=8.0 Hz, 1H), 6.68 (s, 1H), 6.54 (d, J=7.6 Hz, 1H), 6.44 (dd, J=1.6, 8.0 Hz, 1H), 6.27 (t, J=6.0 Hz, 1H), 5.79 (d, J=4.4 Hz, 1H), 4.72-4.68 (m, 1H), 4.25 (d, J=6.0 Hz, 2H), 2.82-2.67 (m, 2H).

Aufarbeitung

  1. customquenched with saturated aqueous NaHCO3
  2. washOrganic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationOrganic layer was concentrated under reduced pressure
  5. customPurification by flash chromatography (40% to 50% EtOAc—hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d23508e709144268b55764c700c95fb6
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674137B2

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