Water → HCID 86709471, compound

HRID 1501781Notes

Reaction equation

HRID 1501781 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.CC1(C)C2[C:41](=[C:42](P(C3C=CC=CC=3)C3C=CC=CC=3)[CH:43]=[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>[CH3:45][CH:44]1[C:43]([N:3]2[CH2:4][CH2:5][C:6]3([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]3)[C:2]2=[O:1])=[CH:42][C:41](=[O:63])[O:40]1

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 86709471HCID 86709471, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of tert-butyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (200 mg, 0.786 mmol), 2-methyl-5-oxo-2,5-dihydrofuran-3-yltrifluoromethanesulfonate (232 mg, 0.944 mmol), Xantphos (45.5 mg, 0.079 mmol), palladium (II) acetate (8.83 mg, 0.039 mmol), water (0.043 mL, 2.359 mmol), and potassium carbonate (217 mg, 1.573 mmol) in toluene (20 mL) was degassed by nitrogen and heated at 65° C. for 16 h. After filtration through CELITE® the filtrate was concentrated and the residue was purified on silica gel column using ethyl acetate and hexane as eluting solvents to give the title compound. LCMS: (M+1)+: 351.15.

Workup

  1. customwas degassed by nitrogen
  2. filtrationAfter filtration through CELITE® the filtrate
  3. concentrationwas concentrated
  4. customthe residue was purified on silica gel column
  5. washas eluting solvents

Sources & evidence

ORD record
ord-fb3b89216de44fb89601d3389f3987ca
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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