Reaktion #442519

Reaktionsgleichung

3-Oxabicyclo[3.2.1]octane-2,4-dione

triethylamine

N-benzyl-O-benzylhydroxylamine hydrochloride

→

product

cis-3-[[(Phenylmethoxy)(phenylmethyl)amino]carbonyl]-cyclopentane carboxylic acid

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedried flask under nitrogen
2. 2
   Sonstigethe reaction is quenched with aqueous citric acid (1M)
3. 3
   ExtraktionExtraction into CH2Cl2 (3×50 mL)
4. 4
   Trocknenby drying over MgSO4
5. 5
   Sonstigeyielded a pale yellow oil, 1.51 g
6. 6
   SonstigeRecrystallization in ethyl acetate/hexane

Vorschrift

552 mg of 3-Oxabicyclo[3.2.1]octane-2,4-dione (3.94 mmol, prepared according to the procedure described in Chem. Lett., p 93, (1994)) is added to a rapidly stirring solution of triethylamine (0.55 mL, 3.94 mmol) and N-benzyl-O-benzylhydroxylamine hydrochloride (983 mg, 3.94 mmol) in CH2Cl2 in a flame dried flask under nitrogen. After stirring at ambient temperature for 3 days, the reaction is quenched with aqueous citric acid (1M). Extraction into CH2Cl2 (3×50 mL), followed by drying over MgSO4, yielded a pale yellow oil, 1.51 g. Recrystallization in ethyl acetate/hexane provided the product as a white crystalline solid, 1.32 g (95%). mp. 118°-120° C.

Quelle