Potassium Bromide → Benzyl 3-formylpiperidine-1-carboxylate

An aqueous solution (2 mL) of potassium bromide (983 mg, 8.26 mmol) was added to 1-benzyloxycarbonyl-3-piperidinyl methanol (2.00 g, 8.02 mmol) and 2,2,6,6-tetramethyl piperidine-N-oxyl (12.5 mg, 0.0802 mmol) in dichloromethane (20 mL). The mixture was stirred for 5 min while chilled in an ice bath. A 0.35 mol/L aqueous sodium hypochlorite solution (25.2 mL, 8.82 mmol) and sodium bicarbonate (1.96 g, 23.3 mmol) were added and the mixture was stirred for 10 min. Subsequently, the reaction mixture was extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.78 g (90%) of the desired compound as a colorless oil.

1. temperaturewhile chilled in an ice bath
2. stirringthe mixture was stirred for 10 min
3. extractionSubsequently, the reaction mixture was extracted with ethyl acetate
4. washthe extract washed with brine
5. dry with materialby drying over magnesium sulfate and evaporation of the solvent
6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

ORD record

ord-6e270006b9de40f4a66816fc7ecc256c

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902367B2