Acetic Acid → HCID 86659879, compound

HRID 2360158Notes

Reaction equation

HRID 2360158 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH3:19])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>C(OCC)(=O)C.O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH:10]([CH3:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 86659878HCID 86659878, compound

Product 1

HCID 86659879HCID 86659879, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-5-methoxy-3-methylindole (200 mg, 0.796 mmol) in a 1:1 solution (2.4 mL) of acetic acid and tetrahydrofuran was added sodium cyanoborohydride (150 mg, 2.38 mmol) at room temperature. After being stirred overnight, sodium cyanoborohydride (50 mg, 0.80 mmol) was added with additional stirring for 6 h. After the reaction mixture was neutralized by saturated NaHCO3 aqueous solution, the reaction mixture was diluted with ethyl acetate. The separated organic layer was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=100/0 to 90/10) to obtain the title compound (62.4 mg, 31%).

Workup

  1. stirringwith additional stirring for 6 h
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100/0 to 90/10)

Sources & evidence

ORD record
ord-ce330384a53f45d4b202e4b4a00fb0f9
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

Loading…