Reaktion #91579

Reaktionsgleichung

3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-oxopropanenitrile

NH4Cl

→

(R)-3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-hydroxypropanenitrile

Lösungsmittel

HCOOH Et3N

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted twice with MTBE
2. 2
   WaschenCombined organic layers were washed with brine
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigePurification by flash chromatography

Vorschrift

(1R,2R)—RuCl(TsDPEN)(p-cymene) (6.3 mg, 0.01 mmol) was added to a degassed solution of 3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-oxopropanenitrile (4) (0.27 g, 1.03 mmol) in HCOOH:Et3N (1:1, 4.0 M in EtOH) and the reaction mixture was stirred at room temperature for 24 hrs. Aqueous NH4Cl (25%) was added and the mixture was extracted twice with MTBE. Combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography gave (R)-3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-hydroxypropanenitrile as an off-white solid which was used directly in the next step. Yield (0.21 g, 77%); 1H NMR (400 MHz, CD3OD) δ 6.64-6.78 (m, 1H), 6.02-6.10 (m, 1H), 4.99-5.09 (m, 1H), 3.79-3.88 (m, 2H), 2.79-2.91 (m, 2H), 1.62-1.90 (m, 6H), 1.12-1.39 (m, 3H), 0.98-1.12 (m, 2H).

Quelle