Water → HCID 21189715, compound

HRID 1068573Notes

Reaction equation

HRID 1068573 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:15])[CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:14][CH2:13][CH2:12][CH:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 21189726HCID 21189726, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21189715HCID 21189715, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(3,4-dimethoxyphenyl)-3-hydroxypropiononitrile (1.25 g, 6.02 mM) in dried tetrahydrofuran (25 ml) was dropped into a solution of lithium aluminum hydride (0.55 g, 14.48 mM) in dried tetrahydrofuran (40 ml) at 0° C. This was gradually warmed to room temperature and stirred for 1 hour. Next, the reaction solution was again cooled to 0° C., water was carefully added to it, then the mixture was stirred at room temperature for 30 minutes. Next, the solution was filtered through Celite, the filtrate was dried over anhydrous sodium sulfate, then the solvent was removed in vacuo to obtain a crude product of 3-amino-1-(3,4-dimethoxyphenyl)-1-propanol (1.27 g). The crude product obtained here had a sufficient purity even without purification, so could be used as it was for the next reaction.

Workup

  1. temperatureNext, the reaction solution was again cooled to 0° C.
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. filtrationNext, the solution was filtered through Celite
  4. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d037efba59ea4226a63945d42c5ada62
Source dataset
uspto-grants-2001_06
Patent number
US06251897B1

Reaction notes

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