Reaction #329720

Reaction equation

1-t-butoxycarbonyl-4-oxohomopiperidine

4-chlorophenylmagnesium bromide

diethyl ether

→

1-t-butoxycarbonyl-4-(4-chlorophenyl)-4-hydroxyhomopiperidine

Yield 96.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherthen quenched with sat'd aqueous NH4Cl (5 mL)
2. 2
   ExtractionThe reaction mixture was extracted with EtOAc (2×50 mL)
3. 3
   Dryingdried over Na2SO4

Procedure

To a cold (0° C.) stirred solution of 1-t-butoxycarbonyl-4-oxohomopiperidine (1.42 g, 6.07 mmol) in anhydrous THF (50 mL) under argon was added dropwise 1.0 M 4-chlorophenylmagnesium bromide in diethyl ether (10 mL, 10 mmol). The reaction was warmed to RT for 2 hrs then quenched with sat'd aqueous NH4Cl (5 mL). The reaction mixture was extracted with EtOAc (2×50 mL), the organic layers combined and dried over Na2SO4. Pure 1-t-butoxycarbonyl-4-(4-chlorophenyl)-4-hydroxyhomopiperidine (2.1 g, 96%) was isolated via silica gel flash chromatography eluting with 50% EtOAc/hexane. 1H NMR CDCl3 δ 1.43 (9H, s), 1.61-2.22 (6H, m), 3.21-3031 (2H, m), 3.48-3.82 (2H, m).

Source