Ammonium formate → HCID 68291585, compound

HRID 713096Notes

Reaction equation

HRID 713096 reaction equation
C([N:8]1[CH2:31][C:12]2([CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH3:30])[CH:21]=3)=[O:19])[CH2:14][CH2:13]2)[O:11][CH:10]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([N:15]2[CH2:14][CH2:13][C:12]3([CH2:31][NH:8][CH2:9][CH:10]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:11]3)[CH2:17][CH2:16]2)=[O:19])=[CH:21][C:22]=1[CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68290983HCID 68290983, compound

Product 1

HCID 68291585HCID 68291585, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To (10-benzyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (264 mg, 0.53 mmol), ammonium formate (167 mg, 2.65 mmol), palladium (30 mg, 0.03 mmol) (10% on carbon) was added methanol (5 mL) and the reaction mixture was stirred at 75° C. for 40 minutes. The reaction mixture was cooled, filtered over celite and concentrated in vacuo. The residue was partitioned between ethyl acetate and 1:1 sat. aq. NaHCO3/25% aq. NaOH, dried over MgSO4, filtered and concentrated in vacuo to give (4-isopropoxy-3-methyl-phenyl)-(8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)methanone (170 mg, 79%), which was used directly without further purification in the next step. ESI-MS m/z calc. 408.5. found 409.7 (M+1)+; Retention time: 1.24 minutes (3 min run).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered over celite and
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and 1:1 sat. aq. NaHCO3/25% aq. NaOH
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0276f89ad03c47679fd22af879d40da6
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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