Reaktion #70829

Reaktionsgleichung

BOP

(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

(±)-(cis)-2-(tert-butoxycarbonylamino)cyclobutanecarboxylic acid

triethylamine

→

title compound

Ausbeute 96.1%

tert-Butyl (±)-(cis)-2-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine-1-carbonyl)cyclobutylcarbamate

Ausbeute 96.1%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAt the conclusion of this period, the solvent was evaporated with a stream of nitrogen
2. 2
   WaschenThe resulting mixture was washed 3× with saturated sodium carbonate, 3× with 1 N HCl
3. 3
   Einengenonce with water, and once with brine, then the organic phase was concentrated in vacuo

Vorschrift

A mixture of (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (91 mg, 0.381 mmol), (±)-(cis)-2-(tert-butoxycarbonylamino)cyclobutanecarboxylic acid (82 mg, 0.381 mmol), and triethylamine (0.186 mL, 1.333 mmol) in methylene chloride (5 mL) was treated with BOP (168 mg, 0.381 mmol), and the mixture was stirred overnight at room temperature. At the conclusion of this period, the solvent was evaporated with a stream of nitrogen, and the resulting residue was taken up in ethyl acetate. The resulting mixture was washed 3× with saturated sodium carbonate, 3× with 1 N HCl, once with water, and once with brine, then the organic phase was concentrated in vacuo to yield the title compound (160 mg, 96% yield) as a colorless glass. The material was used as-is without further purification. MS (ESI+)=437.4 (M+H)+.

Quelle