Reaktion #49226

Reaktionsgleichung

oxazole

n-butyl lithium

( 2 )

(2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

methyl 3-((R)-2-(methoxymethyl)pyrrolidine-1-carbonyl)-5-(oxazol-2-yl)benzoate

tributylstannyl chloride

→

2-(tributylstannyl)oxazole

Lösungsmittel

—

Hexanes

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was warmed up to rt over 3 h
2. 2
   Waschenthe mixture was washed with H2O
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated under vacuum

Vorschrift

Step H (2): Preparation of methyl 3-((R)-2-(methoxymethyl)pyrrolidine-1-carbonyl)-5-(oxazol-2-yl)benzoate. To a solution of oxazole (2.0 g, 29.0 mmol) in THF (30 mL) was added n-butyl lithium (2.0 M solution in cyclohexanes, 16 mL, 31.9 mmol) at −78° C. slowly. The reaction mixture was stirred at −78° C. for 1.2 h, then tributylstannyl chloride (5.0 g, 15.4 mmol) was added. The reaction mixture was warmed up to rt over 3 h. Hexanes (200 mL) was added and the mixture was washed with H2O, dried over Na2SO4 and concentrated under vacuum to give 5.6 g of the 2-(tributylstannyl)oxazole ready for use.

Quelle