Reaktion #357777

Reaktionsgleichung

(3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylic acid

1-[4-(trifluoromethyl)pyridin-2-yl]piperazine

triethylamine

benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate

→

desired product

Ausbeute 29.2%

tert-Butyl [3-(1-Hydroxy-1-methylethyl)-3-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentyl]carbamate

Ausbeute 29.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched by saturated NaHCO3 solution
2. 2
   Extraktionextracted with methylene chloride three times
3. 3
   TrocknenThe combined extracts were dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigepurified by flash column chromatography

Vorschrift

To a suspension of (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylic acid (150 mg, 0.52 mmol) and 1-[4-(trifluoromethyl)pyridin-2-yl]piperazine (130 mg, 0.57 mmol) in methylene chloride (3 mL) under N2 was added triethylamine (0.16 g, 1.6 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.25 g, 0.57 mmol). After being stirred at room temperature overnight, the reaction was quenched by saturated NaHCO3 solution and extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, concentrated and purified by flash column chromatography to yield the desired product (76 mg, 29%).

Quelle