Potassium Carbonate → Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17](OS(C)(=O)=O)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([SH:34])=[CH:30][CH:29]=1)([O-:27])=[O:26]>CN(C=O)C>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH2:16][CH:17]([S:34][C:31]2[CH:32]=[CH:33][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=2)[CH2:18][CH2:19]1)=[O:13])([CH3:8])([CH3:9])[CH3:10]Participants
Conditions
- Temperature
- 70 °C
Procedure
Potassium carbonate (0.45 g, 3.5 mmol) was added in one portion to a stirred solution of 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (0.75 g, 2.5 mmol) and 4-nitrothiophenol (0.5 g, 3.2 mmol) in DMF (25 ml) and the mixture heated to 70° C. for 7 hours. After this time, the reaction mixture was concentrated under vacuum and re-dissolved in ethyl acetate (25 ml) and washed with NaOH (1M solution, 20 ml) and brine (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was purified by column chromatography (elution: 60% heptane, 40% ethyl acetate) to afford the title compound (0.74 g, 68% yield) as an off-white solid. δH (250 MHz, DMSO) 8.14 (2H, d), 7.55 (2H, d), 3.89-3.69 (3H, m), 3.07-2.90 (2H, m), 2.04-1.89 (2H, m), 1.51-1.33 (10H, m).
Workup
- concentrationAfter this time, the reaction mixture was concentrated under vacuum
- dissolutionre-dissolved in ethyl acetate (25 ml)
- washwashed with NaOH (1M solution, 20 ml) and brine (20 ml)
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe resulting residue was purified by column chromatography (elution: 60% heptane, 40% ethyl acetate)
Sources & evidence
- ORD record
- ord-57d3501719b24a2ca7a5b86291f25d61
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946197B2
Reaction notes
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