Potassium Carbonate → Tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 1751054Notes

Reaction equation

HRID 1751054 reaction equation
Cl[C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[C:7](=O)[NH:8][C:4]=2[CH:3]=1.Cl[CH2:26][C:27]1[CH:28]=[C:29]([CH:40]=[CH:41][CH:42]=1)[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].[C:43](=O)([O-])[O-:44].[K+].[K+]>CN(C)C=O>[CH2:33]([O:32][C:30]([C:29]1[CH:28]=[C:27]([CH:42]=[CH:41][CH:40]=1)[CH2:26][N:8]1[C:43](=[O:44])[C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:14][CH2:15]2)[N:6]([C:5]2[CH:23]=[CH:24][CH:2]=[CH:3][CH:4]=2)[CH2:7]1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23024778Benzyl 3-(chloromethyl)benzoateHCID 66652167tert-butyl 4-(5-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 66652022Tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylateYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of tert-butyl 4-(5-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (637 mg, 1.923 mmol, 1 equiv), benzyl 3-(chloromethyl)benzoate (500 mg, 1.923 mmol, 1 equiv) and potassium carbonate (797.3 mg, 5.769 mmol, 3 equiv) in N,N-dimethylformamide was heated at 65° C. for 16 h. The reaction was partitioned between ethyl acetate and water. The organic layer was further washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified using the Biotage flash chromatography system (SNAP, 50 g cartridge, Rf=0.4, gradient—5%-30% ethyl acetate in hexanes) to afford the tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate as an oil (913 mg, 85.6%). MS for C33H37N3O5 m/z 556.27 (M+H)+.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was further washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-64a4e8246e5b4492a993d412d2237da6
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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