Ammonia → HCID 67324738, compound

HRID 1257586Notes

Reaction equation

HRID 1257586 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][C:12](=O)[CH2:13]2)[CH2:8][C:7]1=[O:16].[H][H].[NH3:25]>CO.[Pd]>[NH2:25][CH:12]1[CH2:13][CH:14]2[CH:9]([CH2:8][C:7](=[O:16])[N:6]2[CH2:5][C:4]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 67324479HCID 67324479, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67324738HCID 67324738, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(2,4-Dimethoxy-benzyl)-hexahydro-indole-2,6-dione (47 mg, 0.15 mmol) in 7.0 M of ammonia in methanol (10 mL) was added palladium (10 wt % on activated carbon, 26 mg). The reaction mixture was stirred at room temperature under 1 atm of hydrogen gas for 20 hours. The reaction mixture was then filtered through celite and evaporated in vacuo. Purification by column chromatography on silica gel (gradient: 0 to 5% methanol in dichloromethane containing 2% triethylamine) yielded 28.7 mg (61%) of 6-Amino-1-(2,4-dimethoxy-benzyl)-octahydro-indol-2-one. LCMS (Method E, ESI): RT=0.94 min, m+H=305.2; 1H NMR (400 MHz, CD3OD) δ: 7.11 (d, J=8.3, 1H), 6.52 (d, J=1.7, 1H), 6.50-6.44 (m, 1H), 4.73 (d, J=15.1, 1H), 4.13 (d, J=15.1, 1H), 3.81 (s, 3H), 3.77 (s, 3H), 3.64 (d, J=3.2, 1H), 2.56-2.52 (m, 1H), 2.49 (dd, J=16.5, 6.9, 1H), 2.25 (d, J=14.5, 1H), 2.19 (td, J=11.4, 5.7, 1H), 2.01 (d, J=16.2, 1H), 1.83-1.69 (m, 2H), 1.25 (s, 2H), 1.14 (s, 1H).

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. customevaporated in vacuo
  3. customPurification by column chromatography on silica gel (gradient: 0 to 5% methanol in dichloromethane containing 2% triethylamine)

Sources & evidence

ORD record
ord-a3c6d5e0508b433f8ce4ab96cdb8dd77
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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