HCID 86618154, compound → HCID 68567035, compound

HRID 2246592Notes

Reaction equation

HRID 2246592 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:10][C@H:9]([N:11]([CH3:13])[CH3:12])[CH2:8][CH2:7][C@@H:6]1[N:14]1[CH2:18][CH2:17][C@H:16]([NH:19]C(=O)OCC2C=CC=CC=2)[C:15]1=[O:30])(=[O:3])[CH3:2]>[Pd].CCOC(C)=O>[NH2:19][C@H:16]1[CH2:17][CH2:18][N:14]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([N:11]([CH3:13])[CH3:12])[CH2:10][C@H:5]2[NH:4][C:1](=[O:3])[CH3:2])[C:15]1=[O:30]

Participants

4

Reactant 1

HCID 86618154HCID 86618154, compound

Product 1

HCID 68567035HCID 68567035, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-(dimethylamino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (70 mg) and 10% Pd/C (30 mg of 50% wet catalyst) was added EtOAc (50 mL) and then the flask was evacuated and back-filled with hydrogen. The mixture was stirred under 1 atm H2 for 16 h and the catalyst was removed by filtration through Celite. The filtrate was concentrated in vacuo to give N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(dimethylamino)cyclohexyl)acetamide as a white solid (40 mg, 85% yield), which was taken on to the next step without further purification. LC/MS found [M+H]+=283.

Workup

  1. customthe flask was evacuated
  2. additionback-filled with hydrogen
  3. customthe catalyst was removed by filtration through Celite
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8bae3dbe6abf4196af42d927f0d48c11
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

Loading…