Reaktion #669286

Reaktionsgleichung

2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(R)-phenylmorpholine

methyl 6-bromohexanoate

K2CO3

→

product

Ausbeute 65.0%

2-(S)-(3,5-Bis(trifluoromethyl)benzyloxy)-4-(methoxycarbonylpentyl)-3-(R)-phenylmorpholine

Ausbeute 65.0%

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereaction
2. 2
   TemperaturThe bath temperature was raised to 100° C
3. 3
   TemperaturAfter 3 h the reaction mixture was cooled
4. 4
   WaschenThe EtOAc solution was washed with water (2×), brine
5. 5
   Trocknendried over Na2SO4
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigethe residue was chromatographed

Vorschrift

To a solution of 0.259 g (0.64 mmol) of 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(R)-phenylmorpholine (from example 33) in 2 mL of DMF were added 0.16 g (0.77 mmol) of methyl 6-bromohexanoate, 0.155 g (1.12 mmol) of K2CO3 and 2 crystals of nBu4NI. The resulting solution was heated in a 60° C. bath for 36 h, at which time a tlc indicated incomplete reaction. The bath temperature was raised to 100° C. After 3 h the reaction mixture was cooled and diluted with EtOAc. The EtOAc solution was washed with water (2×), brine and dried over Na2SO4. The filtrate was concentrated and the residue was chromatographed using 30% EtOAc/hexane to isolate 220 mg (65%) of the product.

Quelle