Cesium carbonate → tert-Butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 1848445Notes

Reaction equation

[O:1]=[C:2]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1.FC(F)(F)S(O[C:26]1[CH2:27][O:28][C:29](=[O:32])[C:30]=1[CH3:31])(=O)=O.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:31][C:30]1[C:29](=[O:32])[O:28][CH2:27][C:26]=1[N:3]1[CH2:4][CH2:5][CH2:6][C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[C:2]1=[O:1]

Participants

Conditions

Temperature: 90 °C

Procedure

A microwave vial was charged with commercially available tert-butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate (Shanghai AQ BioPharma Co., Ltd, catalog #ABP3640, 100 mg, 0.373 mmol), 4-methyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (110 mg, 0.447 mmol), Pd2(dba)3 (17 mg, 0.019 mmol), Xantphos (32 mg, 0.056 mmol), and cesium carbonate (182 mg, 0.559 mmol). The vial was sealed, degassed, and filled with toluene (1.5 mL). The reaction mixture was heated at 90° C. overnight, and was filtered through CELITE®. The filtrate was evaporated to give the crude product, which was purified by column chromatography (0-10% MeOH/DCM) to afford the title compound. LC/MS: [(M+1-56)]+=309

Workup

customThe vial was sealed
customdegassed
additionfilled with toluene (1.5 mL)
filtrationwas filtered through CELITE®
customThe filtrate was evaporated
customto give the crude product, which
customwas purified by column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record: ord-e9685b2a2e95443a9fb61ab2a2217a34
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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