Reaction #89089

Reaction equation

Methyl 1-(biphenylcarbonyl)-5-oxopiperidine-2-carboxylate

methyl 1-(biphenylcarbonyl)-5,5-dimethoxypiperidine-2-carboxylate

LiBH4

→

biphenyl-2-yl(2-(hydroxymethyl)-5,5-dimethoxypiperidin-1-yl)methanone

Solvents

THF

Conditions

Workup

1. 1
   OtherThe reaction was carefully quenched with saturated NH4Cl
2. 2
   Extractionextracted with EtOAc
3. 3
   OtherThe organic layer was separated
4. 4
   Dryingdried with MgSO4
5. 5
   Concentrationconcentrated in vacuo

Procedure

Methyl 1-(biphenylcarbonyl)-5-oxopiperidine-2-carboxylate was converted to methyl 1-(biphenylcarbonyl)-5,5-dimethoxypiperidine-2-carboxylate (4.3 mmol, 1.65 g) following the general protocol described in Part I above. To a solution of this ketal in anhydrous THF was added LiBH4 (2M in THF) (9.4 mmol, 4.7 mL) at 0° C. under argon. The resulting mixture was stirred at rt and the reaction was tracked by analytical HPLC. The reaction was carefully quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was separated, dried with MgSO4, and concentrated in vacuo to give desired biphenyl-2-yl(2-(hydroxymethyl)-5,5-dimethoxypiperidin-1-yl)methanone in quantitative yield which was used for next step without further purification.

Source