p-Toluenesulfonic acid monohydrate → HCID 86676456, compound

HRID 1472749Notes

Reaction equation

[OH:1][C:2]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:20]1[CH:24]=[CH:23]SC=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=[O:4].O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(#N)C>[S:38]([C:35]1[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=1)([OH:41])(=[O:40])=[O:39].[CH:20]1([C:2]([OH:1])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:3]([O:5][CH2:6][CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)=[O:4])[CH2:37][CH2:32][CH2:33][CH2:23][CH2:24]1

Participants

Conditions

Temperature: 30 °C

Procedure

To a stirred solution of tert-butyl 4-((2-hydroxy-2-phenyl-2-(thiophen-3-yl)acetyloxy)methyl)piperidine-1-carboxylate (0.84 g, 1.94 mmol) in acetonitrile (10 mL), p-toluenesulfonic acid monohydrate (0.55 g, 2.91 mmol) was added. The reaction was stirred at 30° C. overnight and then concentrated under reduced pressure to afford the title compound (1.17 g, >100%) that was used without further purification in the next step.

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-809be4c204aa47dd830106b84136c13d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012644B2

Reaction notes

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