Reaktion #357761

Reaktionsgleichung

2-piperazin-1-yl-4-(trifluoromethyl)pyrimidine

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

triethylamine

benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate

→

desired product

Ausbeute 55.3%

tert-Butyl [(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)pyrimidin-2-yl]piperazin-1-yl}carbonyl)cyclopentyl]carbamate

Ausbeute 55.3%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with saturated 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%-40% EtOAc/hexanes)

Vorschrift

To a solution of 2-piperazin-1-yl-4-(trifluoromethyl)pyrimidine (250 mg, 1.08 mmol), (1S,3R)-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylic acid (300 mg, 1.1 mmol) and triethylamine (0.45 mL, 3.2 mmol) in methylene chloride (10 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (520 mg, 1.2 mmol). After being stirred overnight, the reaction was quenched with saturated 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%-40% EtOAc/hexanes) provided 290 mg of desired product. MS calculated for C23H34F3N5O3: (M+H) 486; found 386.1 (M-Boc+1).

Quelle