Water → HCID 86709462, compound

HRID 1501772Notes

Reaction equation

HRID 1501772 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.C[C:20]1([CH3:60])[C:46]2[C:41](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=[CH:44][CH:45]=2)[O:40]C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O.C(=O)([O-])[O-:63].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:45]([C:46]1[C:41](=[O:63])[O:40][CH2:60][C:20]=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])[CH3:44]

Participants

7

Reactant 4

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-carboxylate

Product 1

HCID 86709462HCID 86709462, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (200 mg, 0.786 mmol), 4-ethyl-5-oxo-2,5-dihydrofuran-3-yltrifluoromethanesulfonate (246 mg, 0.944 mmol), Xantphos (45.5, 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 60° C. for 16 h. After filtration through CELITE®, the filtrate was concentrated and the residue was purified on silica gel using ethyl acetatehexane to give the title compound. LC/MS: (M+1)+: 365.19.

Workup

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

Sources & evidence

ORD record
ord-081f7e032e9d419d87f3c7c7e481302c
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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