tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 86678665, compound

HRID 1620473Notes

Reaction equation

[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[S:16]=[C:17]1[CH2:21][S:20][C:19](=[O:22])[NH:18]1.CC(C)([O-])C.[K+].C(O)(=O)C.O.C(OCC)(=O)C>C(O)C>[O:22]=[C:19]1[NH:18][C:17](=[S:16])/[C:21](=[CH:1]/[CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)/[S:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-formylpiperidine-1-carboxylate (7.6 g) and 4-thioxo-1,3-thiazolidin-2-one (4.98 g) were suspended in ethanol (200 mL), potassium tert-butoxide (4.80 g) was added, and the reaction mixture was stirred at 80° C. for 4 hr. Acetic acid/water/ethyl acetate were added to the reaction mixture, and the organic layer was separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and washed with diethyl ether to give the title compound (7.8 g).

Workup

customthe organic layer was separated
washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
washwashed with diethyl ether

Sources & evidence

ORD record: ord-9690bea49a354c56b701fe801f265ef5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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