Sodium Bicarbonate → HCID 11325721, compound

HRID 1993474Notes

Reaction equation

HRID 1993474 reaction equation
[NH2:1][C@H:2]1[C:15]2[CH:14]=[C:13]3[C:8]([N:9]=[CH:10][CH:11]=[N:12]3)=[CH:7][C:6]=2[O:5][C:4]([CH3:17])([CH3:16])[C@@H:3]1[OH:18].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO>[CH:15]1([CH2:2][CH2:3][NH:1][C@H:2]2[C:15]3[CH:14]=[C:13]4[C:8]([N:9]=[CH:10][CH:11]=[N:12]4)=[CH:7][C:6]=3[O:5][C:4]([CH3:16])([CH3:17])[C@@H:3]2[OH:18])[CH2:14][CH2:13][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 59134416HCID 59134416, compound

Product 1

HCID 11325721HCID 11325721, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (8R*,9S*)-9-amino-7,7-dimethyl-8,9-dihydro-7H-pyrano[2,3-g]quinoxalin-8-ol (100 mg, 0.408 mmol) in methanol (2 mL), cyclohexylmethyl aldehyde (103 mg, 0.816 mmol) was added, and the resulting mixture was stirred at room temperature for 20 minutes. Sodium cyanoborohydride (51 mg, 0.816 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 1 hour. Upon the completion of the reaction, saturated sodium hydrogencarbonate aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried over magnesium sulfate and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=2/1) to obtain the aimed product (yield: 48%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. additionwas added
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-5ee73f5ae5a04e78bab3daea1af88746
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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