Sodium Bicarbonate → HCID 21090534, compound

HRID 350846Notes

Reaction equation

HRID 350846 reaction equation
[CH2:1]1[CH2:15][O:14][C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH2:4][CH2:5][CH2:6][NH2:7])[O:2]1.[CH:16]([C:18]1[CH:19]=[C:20]([CH:32]=[CH:33][CH:34]=1)[O:21][CH:22]([CH2:30][CH3:31])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:15]1[CH2:1][O:2][C:3]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([CH2:4][CH2:5][CH2:6][NH:7][CH2:16][C:18]2[CH:19]=[C:20]([CH:32]=[CH:33][CH:34]=2)[O:21][CH:22]([CH2:30][CH3:31])[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[O:14]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21090531Tert-butyl 2-(3-formylphenoxy)butyrateHCID 23123945HCID 23123945, compound

Product 1

HCID 21090534HCID 21090534, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4,4-Ethylenedioxy-4-phenylbutylamine (27.0 mg, 0.13 mmol) was dissolved in chloroform (3 ml) at room temperature, and thereto were added tert-butyl 2-(3-formylphenoxy)butyrate (34.4 g, 0.13 mmol) in a chloroform solution (2 ml) and sodium triacetoxyborohydride (41.4 mg, 0.20 mmol) in sequential order at the same temperature, and thereafter, the mixture was stirred at room temperature for 12 hours. The reaction solution was added to a saturated aqueous sodium hydrogencarbonate solution and thereafter extracted by chloroform. The extracted organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained as a colorless oil (38.5 mg, 64.9%).

Workup

  1. extractionextracted by chloroform
  2. washThe extracted organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound

Sources & evidence

ORD record
ord-a8c0842e0d00484db45e97702a90412a
Source dataset
uspto-grants-2007_02
Patent number
US07183295B2

Reaction notes

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