HCID 18007303, compound → 3-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amine

HRID 1351902Notes

Reaction equation

HRID 1351902 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([NH:12]CC3C=CC=CC=3)[CH2:11][C:5]=2[CH:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([NH2:12])[CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 18007303HCID 18007303, compound

Product 1

HCID 180073203-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-amineYield 29.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[(2R)-3-(3-methylsulfonylamino-4-benzyloxy)phenyl-2-hydroxypropyl]-N-[(6RS)-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)benzylamine (34 mg), 50% wet palladium (10%) on charcoal (10 mg) and methanol (1 ml) was stirred under hydrogen (1 atm) at room temperature for 1.5 hours. The reaction mixture was filtered and evaporated. The residue was purified by preparative TLC (eluent; 25% methanol-dichloromethane) to give N-[(2R)-3-(3-methylsulfonylamino-4-hydroxy)phenyl-2-hydroxypropyl]-[(6RS)-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]amine (6.9 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customThe residue was purified by preparative TLC (eluent; 25% methanol-dichloromethane)

Sources & evidence

ORD record
ord-2dcef0343bc64a798be62c9587190b34
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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