Methanol → 4-[2-(4-Methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([C:23]3[CH:28]=[CH:27][C:26](SC)=[CH:25][CH:24]=3)[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[O:32][S:33]([O-:35])=O.[K+].[CH3:37]O>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2([C:23]3[CH:28]=[CH:27][C:26]([S:33]([CH3:37])(=[O:35])=[O:32])=[CH:25][CH:24]=3)[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 887Methanol

HCID 23707502Potassium hydroxy sulfite2×

HCID 689712404-[2-(4-Methylsulfanyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689706894-[2-(4-Methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine-1-carboxylic acid tert-butyl esterYield 100%

Procedure

To 4-[2-(4-methylsulfanyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 272) (166 mg, 0.375 mmol) in MeOH (5 mL) cooled to 0° C. was added OXONE® (461 mg, 0.75 mmol) and the mixture was stirred at room temperature for 2 hours. A second aliquot of OXONE® (461 mg, 0.75 mmol) was added and the mixture stirred at room temperature for 24 hours. Standard work-up gave 4-[2-(4-methanesulfonyl-phenyl)-benzo[1,3]dioxol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (172 mg, 100%).