Methanol → HCID 18477100, compound

HRID 2188212Notes

Reaction equation

HRID 2188212 reaction equation
[CH2:1]([CH2:8][NH:9][CH2:10][C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21]C)[CH:17]=2)[C:12]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>ClCCl>[CH2:1]([CH2:8][NH:9][CH2:10][C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[C:12]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18477137HCID 18477137, compound

Product 1

HCID 18477100HCID 18477100, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(N-benzylmethylamino)methyl-6-methoxy-1-phenyl-3,4-dihydronaphthalene (0.375 g; prepared according to Process 1) in dichloromethane (15 cm3) being stirred at 0° C. under nitrogen was added a solution of boron tribromide in dichloromethane (1 M, 2.2 cm3). The resulting solution was stirred at 0° C. for 30 min and then at room temperature for 1.5 h. Methyl alcohol (5 cm3) was added and the solvents were removed under reduced pressure. The residue was treated with hydrochloric acid (6 M, 2 cm3) and dichloromethane (4 cm3) and stirred at room temperature for 30 min. The mixture was basified with potassium carbonate, diluted with water (50 cm3), and extracted with dichloromethane (3×25 cm3). The combined organic extracts were washed with brine (25 cm3), dried (MgSO4), and the solvent was removed under reduced pressure. The crude product was purified by column chromatography [silica, eluting with ethyl acetate-heptane (1:1)] to yield the title compound (0.202 g) as a brown oil.

Workup

  1. waitat room temperature for 1.5 h
  2. customthe solvents were removed under reduced pressure
  3. additionThe residue was treated with hydrochloric acid (6 M, 2 cm3) and dichloromethane (4 cm3)
  4. stirringstirred at room temperature for 30 min
  5. additiondiluted with water (50 cm3)
  6. extractionextracted with dichloromethane (3×25 cm3)
  7. washThe combined organic extracts were washed with brine (25 cm3)
  8. dry with materialdried (MgSO4)
  9. customthe solvent was removed under reduced pressure
  10. customThe crude product was purified by column chromatography [silica, eluting with ethyl acetate-heptane (1:1)]

Sources & evidence

ORD record
ord-13aeb212670e4c11b552463b089775ce
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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