HCID 58597290, compound → HCID 58597284, compound

HRID 1444701Notes

Reaction equation

HRID 1444701 reaction equation
[N:1]([C@H:4]1[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:8]=2[CH2:7][CH2:6][CH2:5]1)[CH2:15][N:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]3)=[N+]=[N-]>CCOC(C)=O.CO.[Pd]>[CH2:18]([N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][C:8]3[CH2:7][CH2:6][CH2:5][C@@H:4]([NH2:1])[C:9]=3[CH:10]=2)[CH2:15]1)[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 1

HCID 58597290HCID 58597290, compound

Product 1

HCID 58597284HCID 58597284, 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)-6-azido-2-isobutyl-1,2,3,4,6,7,8,9-octahydrobenzo[g]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)-2-isobutyl-1,2,3,4,6,7,8,9-octahydrobenzo[g]isoquinolin-6-amine as a colorless oil.

Sources & evidence

ORD record
ord-480f6eb4242e479f99bb40eba811f7d4
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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