Water → HCID 86610917, compound

HRID 335004Notes

Reaction equation

HRID 335004 reaction equation
C(O[C:4](=O)[CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[C:12](C)[CH:11]=[C:10]([CH3:15])[CH:9]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:23].C(Cl)Cl.[CH3:27]O>O1CCCC1>[CH3:27][CH2:4][CH2:5][CH:6]([NH:7][C:8]1[CH:9]=[C:10]([CH3:15])[CH:11]=[CH:12][CH:13]=1)[OH:23]

Participants

6

Reactant 4

HCID 962WaterHCID 21226129Dichloromethane methanolHCID 21226445Aluminium lithium hydrideHCID 23052938HCID 23052938, compound

Product 1

HCID 86610917HCID 86610917, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

3-(3,5-dimethyl-phenylamino)-propionic acid ethyl ester (0.00226 mol) in tetrahydrofuran (5 ml) was added drop wise to a slurry of LiAlH4 (0.0034 mol) in tetrahydrofuran (10 ml) at 5° C. under N2 flow. The mixture was stirred at 5° C. for 1 hour. A minimum of water and CH2Cl2/CH3OH (95/5) were added. The solution was dried (over MgSO4), filtered and the solvent was evaporated until dryness, yielding 0.35 g of 3-(3,5-dimethyl-phenylamino-propan-1-ol (86%). 5-(3,5-dimethyl-phenylamino)-pentan-1-ol was prepared analogously.

Workup

  1. dry with materialThe solution was dried (over MgSO4)
  2. filtrationfiltered
  3. customthe solvent was evaporated until dryness

Sources & evidence

ORD record
ord-e19d0350c0f34f1294cb171c176436e3
Source dataset
uspto-grants-2014_11
Patent number
US08883837B2

Reaction notes

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