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

HRID 2299689Notes

Reaction equation

HRID 2299689 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-52e40e41d1794eb1bca6aab880ad1ff3
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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