Potassium Carbonate → HCID 69448964, compound

HRID 1593021Notes

Reaction equation

[CH2:1]([CH:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]1=[O:9])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CS(O[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)(=O)=O>CN(C=O)C>[CH2:1]([CH:3]1[C:4](=[O:9])[N:5]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[C:6](=[O:8])[NH:7]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-ethylimidazoline-2,4-dione (1 g) in DMF (40 ml) was added potassium carbonate (2.16 g) followed by tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (2.18 g) and the resulting mixture was heated to 100° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and then was partitioned between dichloromethane and water. The organic layer was collected, dried and evaporated to dryness. The residue was purified by chromatography on silica eluting with a gradient of isohexane to ethyl acetate/isohexane (1:1) to give tert-butyl 4(4-ethyl-2,5-dioxoimidazolidin-1-yl)piperidine-1-carboxylate as a solid. Yield 1.12 g. NMR (CDCl3): 0.95 (t, 3H), 1.5 (s, 9H), 1.9 (m, 2H), 2.35 (m, 2H), 2.7 (m, 2H), 3.8-4.0 (m, 3H), 4.1 (q, 2H), 5.6 (bs, 1H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customwas partitioned between dichloromethane and water
customThe organic layer was collected
customdried
customevaporated to dryness
customThe residue was purified by chromatography on silica eluting with a gradient of isohexane to ethyl acetate/isohexane (1:1)

Sources & evidence

ORD record: ord-efe153da3f394f4e9f915650a34ede32
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294636B2

Reaction notes

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