Acetic Acid → HCID 66760565, compound

HRID 1850414Notes

Reaction equation

HRID 1850414 reaction equation
C=O.[Br:3][C:4]1[C:5]([CH3:18])=[C:6]([CH3:17])[C:7]2[O:11][C:10]([CH2:13]N)([CH3:12])[CH2:9][C:8]=2[C:15]=1[CH3:16].[C:19](O)(=O)C.[C:23]([BH3-])#[N:24].[Na+].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CO>[Br:3][C:4]1[C:5]([CH3:18])=[C:6]([CH3:17])[C:7]2[O:11][C:10]([CH2:13][N:24]([CH3:23])[CH3:19])([CH3:12])[CH2:9][C:8]=2[C:15]=1[CH3:16]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66758777HCID 66758777, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66760565HCID 66760565, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

37% formalin aqueous solution (0.5 mL) was added to a solution of methanol (6 mL) containing 1-(5-bromo-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanamine (250 mg, 0.880 mmol) synthesized in Reference Example 129, acetic acid (140 mg, 2.33 mmol) and sodium cyanoborohydride (98 mg, 1.56 mol) under ice-cooling condition. The mixture was warmed to room temperature and stirred for 15 hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution to separate an organic layer. The organic layer was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by basic silica gel chromatography (hexane-ethyl acetate 97:3-88:12) to give 220 mg of the title compound (yield: 80%).

Workup

  1. temperaturecooling condition
  2. customto separate an organic layer
  3. washThe organic layer was washed with saturated saline
  4. customdried
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe residue was purified by basic silica gel chromatography (hexane-ethyl acetate 97:3-88:12)

Sources & evidence

ORD record
ord-032249648f6940febeb70b4818e45ab5
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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