Reaktion #357769

Reaktionsgleichung

4-piperazin-1-yl-6-(trifluoromethyl)pyrimidine

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

benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate

triethylamine

→

desired product

Ausbeute 38.3%

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

Ausbeute 38.3%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine
2. 2
   Trocknendried with sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe crude residue was purified by flash column chromatography

Vorschrift

A solution of 4-piperazin-1-yl-6-(trifluoromethyl)pyrimidine (1.0 g, 4.31 mmol), (1S,3R)-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylic acid (1.75 g, 6.46 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.86 g, 6.46 mmol), and triethylamine (1.20 mL, 8.61 mmol) in methylene chloride (10 mL) was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (800 mg, 38.3%). LCMS calculated for C23H35F3N5O3: (M+1) 486.2; found 486.2.

Quelle