tert-Butyl 4-oxopiperidine-1-carboxylate → 4-(4-Benzenesulfonyl-2-hydroxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

To a solution of 2-amino-5-benzenesulfonyl-phenol (1.00 g., 4.016 mmol) in 20 mL dichlormethane was added 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.880 g, 4.418 mmol) followed by sodium triacetoxyborohydride (1.78 g, 8.43 mmol) and the resulting suspension was stirred at room temperature under nitrogen for 24 hours. The reaction mixture was washed twice with 50 mL water, once with 50 mL brine, then dried over sodium sulfate and concentrated in vacuo. The resulting crude solid was purified by flash chromatography (20-30% ethyl acetate in hexanes) to give 1.823 g (4.53 mmol, 94%) of 4-(4-benzenesulfonyl-2-hydroxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester as a foam. MS: 333 (M−CO2tBu+H)+, 377 (M−tBu+H)+.

1. washThe reaction mixture was washed twice with 50 mL water, once with 50 mL brine
2. dry with materialdried over sodium sulfate
3. concentrationconcentrated in vacuo
4. customThe resulting crude solid was purified by flash chromatography (20-30% ethyl acetate in hexanes)

ORD record

ord-d3350447ef554b37b84bd26a438160c0

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378415B2