Sodium Bicarbonate → HCID 59134407, compound

HRID 2425350Notes

Reaction equation

HRID 2425350 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 sodium hydrogencarbonate aqueous 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-864f7bd1ca8a43d880cd7ac3b42c7f3d
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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