2-Tetralone → HCID 15078242, compound

HRID 1110445Notes

Reaction equation

HRID 1110445 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]1[C:26](=O)[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1.C([BH3-])#N.[Na+]>CO>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][CH:21]2[CH2:22][CH2:23][C:24]3[C:19](=[CH:18][CH:17]=[CH:26][CH:25]=3)[CH2:20]2)=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 682662-TetraloneHCID 27238314-Benzyloxyaniline hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15078242HCID 15078242, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.00 g (4.2 mmol, Aldrich) of 4-benzyloxyaniline hydrochloride, 560 μl (4.24 mmol, Aldrich) of β-tetralone and 132 mg (2.10 mmol) of sodium cyanoborohydride in 30 ml of MeOH over 3A molecular sieves was stirred at room temperature for 2.5 hours. The mixture was filtered, EtOAc was added and this was washed with saturated NaHCO3 twice. The organic layer was dried (MgSO4) and concentrated in vacuo. Purification via flash chromatography (silica gel, 1:10 EtOAc/petroleum ether) afforded 1.28 g (93%) of title compound as a golden yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. additionEtOAc was added
  3. washthis was washed with saturated NaHCO3 twice
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (silica gel, 1:10 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-dbe8b9b184f445dc98fb54d2003a8b43
Source dataset
uspto-grants-1990_12
Patent number
US04975461

Reaction notes

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