Water → HCID 86709466, compound

HRID 1501776Notes

Reaction equation

HRID 1501776 reaction equation
[O:1]=[C: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)[CH2:5][CH2:4][NH:3]1.FC(F)(F)S(O[C:25]1[CH2:26][O:27][C:28](=[O:33])[C:29]=1[CH:30]([CH3:32])[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.O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:30]([C:29]1[C:28](=[O:33])[O:27][CH2:26][C:25]=1[N:3]1[CH2:4][CH2:5][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:2]1=[O:1])([CH3:32])[CH3:31]

Participants

8

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 45073946tert-Butyl 1-oxo-2,8-diazaspiro(4.5)decane-8-carboxylateHCID 86709465HCID 86709465, compound

Product 1

HCID 86709466HCID 86709466, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
66 °C

Procedure

A mixture of tert-butyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (I-11) (200 mg, 0.786 mmol), 4-isopropyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (259 mg, 0.944 mmol), Xantphos (46 mg, 0.079 mmol), palladium (II) acetate (8.8 mg, 0.039 mmol), water (0.043 mL, 2.4 mmol), and potassium carbonate (217 mg, 1.57 mmol) in toluene (20 mL) was heated at 66° C. for 16 h. After filtration through CELITE®, the filtrate was concentrated and the residue was purified on a silica gel column to give the title compound. LC/MS: (M+1)+: 379.21.

Workup

  1. filtrationAfter filtration through CELITE®
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-61dfb4f36be1481fa1b357133775eb95
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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