Ethyl 2-[3-(benzylamino)-1,1-dioxo-thietan-3-yl]acetate → Ethyl (3-amino-1,1-dioxido-3-thietanyl)acetate

HRID 1480234Notes

Reaction equation

C([NH:8][C:9]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][S:11](=[O:14])(=[O:13])[CH2:10]1)C1C=CC=CC=1>CCO.[Pd]>[NH2:8][C:9]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][S:11](=[O:14])(=[O:13])[CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 2-[3-(benzylamino)-1,1-dioxo-thietan-3-yl]acetate (example 160b, 0.5 g, 1.68 mmol) in EtOH (12.5 ml) under an argon atmosphere was added palladium on charcoal 10% (w/w 10%) (50.0 mg, 470 μmol). The reaction flask was put under a pressure of 2.5 bar H2 and the reaction mixture was then stirred at 50° C. for 16 hours. Palladium catalyst was removed by filtration over a pad of Celite and the filter cake was washed with ethanol twice. The filtrate was evaporated down to dryness to yield the title compound (350 mg, 100%) as a crude product which was used without any purification. MS (ESI, m/z): 208.1 (M+H+).

Workup

customPalladium catalyst was removed by filtration over a pad of Celite
washthe filter cake was washed with ethanol twice
customThe filtrate was evaporated down to dryness

Sources & evidence

ORD record: ord-6894de9514cb4ea6a5b417cd337cfff2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Reaction notes

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