Reaction #309157

Reaction equation

ammonium chloride

benzylmagnesium chloride

tert-butyl [2-(4-cyanophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]carbamate

isopropylmagnesium chloride

THF

→

tert-butyl {2-[4-(phenylacetyl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate

Conditions

Workup

1. 1
   Extractionextracted with EtOAc
2. 2
   Dryingdried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   OtherThe crude residue was purified by column chromatography
6. 6
   Washeluting with 1-60% EtOAc/Hexane
7. 7
   Otherthe solvent removed in vacuo

Procedure

To a solution of tert-butyl [2-(4-cyanophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]carbamate (1-6) (15.0 g, 45.4 mmol) in THF (150 mL) at −78° C. was added isopropylmagnesium chloride (22.7 mL, 45.4 mmol, 2M in THF). After 1 hour, benzylmagnesium chloride (68 mL, 135 mmol, 2M in THF) was added and the reaction was allowed to slowly warm to rt over 5 hours. The reaction mixture was poured into saturated ammonium chloride, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by column chromatography eluting with 1-60% EtOAc/Hexane. The appropriate fractions were combined and the solvent removed in vacuo to give tert-butyl {2-[4-(phenylacetyl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate (1-7). MS (M+H)+: 424.

Source