6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-one → HCID 15078224, compound

HRID 1110447Notes

Reaction equation

HRID 1110447 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.Cl.[CH2:15]([O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH3-]C#N.[Na+]>CO>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([NH:27][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)=[CH:28][CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 27238314-Benzyloxyaniline hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15078224HCID 15078224, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 977 mg (S.54 mmol, Aldrich) of 6-methoxy-2-tetralone, 1.30 g (5.54 mmol, Aldrich) of 4-benzyloxyaniline hydrochloride and 174 mg (2.77 mmol, Aldrich) of NaBH3CN in 30 ml of MeOH was stirred at 25° C. over 3A molecular sieves for 1.75 hour. The mixture was filtered, saturated NaHCO3 was added and this was extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated in vacuo. Purification via flash chromatography (silica gel, 1:8 EtOAc/petroleum ether) afforded 1.36 g (69%) of title compound as a deep red oil.

Workup

  1. filtrationThe mixture was filtered
  2. additionsaturated NaHCO3 was added
  3. extractionthis was extracted with EtOAc
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (silica gel, 1:8 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-9481522ea2bf4242927e0b836956cef6
Source dataset
uspto-grants-1990_12
Patent number
US04975461

Reaction notes

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