Reaktion #357765

Reaktionsgleichung

1-[6-(trifluoromethyl)pyridin-2-yl]piperazine

(1S,3R)-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylic acid

triethylamine

benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate

→

desired product

Ausbeute 59.2%

tert-Butyl [(1R,3S)-3-isopropyl-3-(4-[6-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopentyl]carbamate

Ausbeute 59.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with saturated sodium NaHCO3
2. 2
   ExtraktionThe resulting solution was extracted with EtOAc three times
3. 3
   TrocknenThe combined organic layers were dried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigePurification by column chromatography on silica gel (20% EA/hex to 40% EA/hexanes)

Vorschrift

To a solution of 1-[6-(trifluoromethyl)pyridin-2-yl]piperazine (249 mg, 1.08 mmol), (1S,3R)-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylic acid (300 mg, 1.10 mmol), triethylamine (0.45 mL, 3.2 mmol) in methylene chloride (10 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (524 mg, 1.18 mmol). After being stirred overnight, the reaction was quenched with saturated sodium NaHCO3. The resulting solution was extracted with EtOAc three times. The combined organic layers were dried (MgSO4) and concentrated. Purification by column chromatography on silica gel (20% EA/hex to 40% EA/hexanes) provided 310 mg of the desired product. MS calculated for C24H36F3N4O3: (M+H) 485.3; found 485.3.

Quelle