Water → HCID 59479038, compound

HRID 450761Notes

Reaction equation

HRID 450761 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[N:2].O.[BH4-].[Na+]>C1COCC1.CO.[Co](Cl)Cl>[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10]

Participants

7

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86645196HCID 86645196, compound

Product 1

HCID 59479038HCID 59479038, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g of tert-butyl [3-(cyanomethyl)phenoxy]acetate in 20 ml of THF and 10 ml of methanol was added dropwise a suspension of 1.31 g of cobalt chloride and 20 ml of water, and then 459 mg of sodium borohydride was portionwise added thereto at room temperature. After stirring at room temperature for 10 minutes, the insoluble material was separated by filtration over Celite, washed with methanol, and then concentrated. The obtained residue was extracted with chloroform, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated. The obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol-saturated aqueous ammonia) to obtain 632 mg of tert-butyl [3-(2-aminoethyl)phenoxy]acetate as a pale yellow oily substance.

Workup

  1. customat room temperature
  2. customthe insoluble material was separated by filtration over Celite
  3. washwashed with methanol
  4. concentrationconcentrated
  5. extractionThe obtained residue was extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was then evaporated
  8. customThe obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol-saturated aqueous ammonia)

Sources & evidence

ORD record
ord-382892ce2a14427bb6dda26526a24105
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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