Trimethylsilyl cyanide → (S)-2-((R)-2-hydroxy-1-phenylethylamino)-2-(1-methylcyclopropyl)acetonitrile

HRID 520355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520355
[CH3:1][C:2]1([CH:5]=O)[CH2:4][CH2:3]1.[NH2:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][OH:10].C[Si]([C:21]#[N:22])(C)C>CO>[OH:10][CH2:9][C@H:8]([NH:7][C@@H:5]([C:2]1([CH3:1])[CH2:3][CH2:4]1)[C:21]#[N:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 82115Trimethylsilyl cyanideHCID 2724025(R)-beta-aminophenethyl alcoholHCID 101976191-Methylcyclopropane-1-carbaldehyde

Produkt 1

HCID 86690076(S)-2-((R)-2-hydroxy-1-phenylethylamino)-2-(1-methylcyclopropyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-methylcyclopropanecarbaldehyde in MeOH (20 mL) was added (R)-2-amino-2-phenylethanol (3.23 g, 23.54 mmol) at rt under N2 in 3 portions. The mixture was stirred at rt for 2 h and then cooled down with ice-water bath and added with trimethylsilyl cyanide (5.74 mL, 42.8 mmol) dropwise over 5 min. The mixture was stirred for 10 min, ice bath was removed and the reaction was stirred at rt overnight. The reaction mixture was concentrated and purified on a 40 g silica gel column (EtOAc/hexane: 0 to 100%) to afford (S)-2-((R)-2-hydroxy-1-phenylethylamino)-2-(1-methylcyclopropyl)acetonitrile. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.40-7.30 (m, 5H), 4.08 (dd, J=9.2, 4.1 Hz, 1H), 3.82 (dd, J=10.8, 4.0 Hz, 1H), 3.64 (t, J=10.0 Hz, 1H), 2.97 (s, 1H), 1.26 (s, 3H), 0.63-0.53 (m, 2H), 0.51-0.42 (m, 2H).

Aufarbeitung

  1. temperaturecooled down with ice-water bath
  2. stirringThe mixture was stirred for 10 min
  3. customice bath was removed
  4. stirringthe reaction was stirred at rt overnight
  5. concentrationThe reaction mixture was concentrated
  6. custompurified on a 40 g silica gel column (EtOAc/hexane: 0 to 100%)

Quellen und Nachweise

ORD-Eintrag
ord-3c7d8aaeb009425fae92efd3b5df1c62
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326973B2

Notizen zur Reaktion

Wird geladen…