HCID 58597258, compound → HCID 58597253, compound

HRID 1444695Notes

Reaction equation

HRID 1444695 reaction equation
[N:1]([C@H:4]1[C:17]2[CH:16]=[CH:15][C:14]3[CH2:13][N:12]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:11][CH2:10][C:9]=3[C:8]=2[CH2:7][CH2:6][CH2:5]1)=[N+]=[N-]>CCOC(C)=O.CO.[Pd]>[CH2:18]([N:12]1[CH2:11][CH2:10][C:9]2[C:8]3[CH2:7][CH2:6][CH2:5][C@@H:4]([NH2:1])[C:17]=3[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 1

HCID 58597258HCID 58597258, compound

Product 1

HCID 58597253HCID 58597253, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

A suspension of 30 mg of Pd/C (10% w/w) in a solution of (R)-7-azido-3-isobutyl-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinoline (296 mg, 1 mmol) in 30 mL of EtOAc was stirred under H2 atmosphere overnight. The reaction mixture was then directly submitted to flash chomatograph (SiO2, EtOAc to EtOAc/2M NH3 in MeOH=100:15 to 100:25 to 100:35) to give (R)-3-isobutyl-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinolin-7-amine as a colorless oil.

Sources & evidence

ORD record
ord-3d50e3e63d9c4be68a792a6cd9aec5b4
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

Loading…