Ammonium Chloride → (R)-3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-hydroxypropanenitrile

HRID 63301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63301
[CH:1]1([CH2:7][O:8][C:9]2[S:13][C:12]([C:14](=[O:18])[CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+].[Cl-]>C(O)=O.CCN(CC)CC>[CH:1]1([CH2:7][O:8][C:9]2[S:13][C:12]([C@H:14]([OH:18])[CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 25517Ammonium ChlorideHCID 866945893-(5-(Cyclohexylmethoxy)thiophen-2-yl)-3-oxopropanenitrile

Produkt 1

HCID 86694588(R)-3-(5-(cyclohexylmethoxy)thiophen-2-yl)-3-hydroxypropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11084032Triethylammonium formateLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

  1. extractionthe mixture was extracted twice with MTBE
  2. washCombined organic layers were washed with brine
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0860ce323f6e4fe1b554e30e5703835e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447078B2

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