Nitrogen → HCID 86709516, compound

HRID 1501819Notes

Reaction equation

[OH:1][CH:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:5](=[O:19])[NH:4][CH:3]1[CH3:20].C[C:22]1([CH3:62])[C:48]2[C:43](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:42]C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=[O:64].[K+].[K+].N#N.O>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[OH:1][CH:2]1[C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:10][CH2:11]2)[C:5](=[O:19])[N:4]([C:22]2[CH2:62][O:42][C:43](=[O:64])[CH:48]=2)[CH:3]1[CH3:20]

Participants

Conditions

Temperature: 90 °C

Procedure

To a round bottom flask was charged tert-butyl 4-hydroxy-3-methyl-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (1000 mg, 3.52 mmol), 4-bromofuran-2(514)-one (860 mg, 5.28 mmol), Pd(OAc)2 (79 mg, 0.352 mmol), Xantphos (305 mg, 0.528 mmol), and K2CO3 (972 mg, 7.03 mmol). The flask was sealed, vacuumed and back filled with N2 and filled with dioxane (14 mL) and water (190 μL, 10.6 mmol). The reaction mixture was heated at 90° C. overnight, and filtered through CELITE®. The filtrate was evaporated to give the crude product, which was purified by column chromatography (0-10% MeOH/DCM, came out at 6% MeOH/DCM, followed by another column with 0-100% EtOAc/hex) to give the title compound. LCMS: [(M+1)]+=367

Workup

customThe flask was sealed
filtrationfiltered 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-7b676f9819c94b79bc51438c61455690
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206198B2

Reaction notes

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