Sodium Bicarbonate → HCID 59134407, compound

HRID 1993469Notes

Reaction equation

HRID 1993469 reaction equation
N[C@H:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:9]([CH3:17])=[CH:10][C:11]([Cl:16])=[N:12][C:13]=3[CH:14]=2)[O:5][C:4]([CH3:19])([CH3:18])[C@@H:3]1[OH:20].[C:21]([BH3-])#[N:22].[Na+].C(=O)([O-])O.[Na+]>CO>[Cl:16][C:11]1[CH:10]=[C:9]([CH3:17])[C:8]2[CH:7]=[C:6]3[O:5][C:4]([CH3:19])([CH3:18])[C@H:3]([OH:20])[C@@H:2]([NH:22][CH2:21][CH2:15][CH2:2][CH2:3][CH3:4])[C:15]3=[CH:14][C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 59134312HCID 59134312, compound

Product 1

HCID 59134407HCID 59134407, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3R*,4S*)-4-amino-7-chloro-2,2,9-trimethyl-3,4-dihydro-2H-pyrano[2,3-g]quinolin-3-ol (60 mg, 0.205 mmol) in methanol (1.2 mL), butyl aldehyde (35 mg, 0.041 mmol) was added, and the resulting mixture was stirred at room temperature for 20 minutes. Sodium cyanoborohydride (52 mg, 0.82 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 1 hour. Upon the completion of the reaction, saturated aqueous sodium hydrogencarbonate solution was added thereto, and 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=3/1) to obtain the aimed product (yield: 41%).

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=3/1)

Sources & evidence

ORD record
ord-1cc35989f45b4f7e809a73c266dc7fd4
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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