Diisopropylethylamine → tert-Butyl 2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 1848439Notes

Reaction equation

Br[C:2]1[CH2:6][O:5][C:4](=[O:7])[CH:3]=1.CCN(C(C)C)C(C)C.[CH2:17]1[C:22]2([CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH2:21][CH2:20][N:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:18]1>C1COCC1>[O:7]=[C:4]1[O:5][CH2:6][C:2]([N:24]2[CH2:25][CH2:26][CH2:27][C:22]3([CH2:17][CH2:18][N:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20][CH2:21]3)[CH2:23]2)=[CH:3]1

Participants

Conditions

Temperature: 76 °C

Procedure

To commercially available 4-bromofuran-2(5H)-one (128 mg, 0.786 mmol) in THF (4 mL) was added Hunig's Base (275 μL, 1.57 mmol) and tert-butyl 3,8-diazaspiro[5,5]undecane-3-carboxylate (200 mg, 0.786 mmol). The reaction mixture was stirred at 76° C. overnight, concentrated and purified by column chromatography (0-10% MeOH in DCM) to afford the title compound. LC/MS: [(M+1)]+=337

Workup

concentrationconcentrated
custompurified by column chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-65d668ee041a4bdc86bac3e8b31a3281
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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