Water → HCID 118179068, compound

HRID 1050731Notes

Reaction equation

HRID 1050731 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][NH2:26].[BH4-].[Na+].O>C(O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][NH:26][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 748962-MethoxyphenethylamineHCID 4311764Sodium borohydrideHCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 118179068HCID 118179068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.2 g (74.5 mmol) of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate [U. Gerlach and T. Wollmann, Tetrahedron Lett. 1992, 33 (38), 5499-5502] and 11.5 g (74.5 mmol) of 2-(2-methoxyphenyl)ethylamine in 50 ml of ethanol were heated under reflux for 2 h. The mixture was then concentrated to dryness under reduced pressure, the residue was taken up in 300 ml of methanol and 5.6 g (149 mmol) of sodium borohydride were, over 20 min, added a little at a time at RT with slight external cooling to the suspension. The brownish solution was stirred at RT for 24 h and then poured into 900 ml of water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated. The residue (24.5 g) was purified by flash chromatography on silica gel using the mobile phase cyclohexane/ethyl acetate 2:1.

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationThe mixture was then concentrated to dryness under reduced pressure
  3. additionadded a little at a time at RT with slight
  4. temperatureexternal cooling to the suspension
  5. extractionextracted three times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. concentrationconcentrated
  8. customThe residue (24.5 g) was purified by flash chromatography on silica gel using the mobile phase cyclohexane/ethyl acetate 2:1

Sources & evidence

ORD record
ord-fd7f25770acc436ea67ea7a5aec70299
Source dataset
uspto-grants-2016_07
Patent number
US09387203B2

Reaction notes

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