Water → HCID 86734673, compound

HRID 328873Notes

Reaction equation

HRID 328873 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([CH:25]([OH:31])[CH2:26][NH:27][CH:28]([CH3:30])[CH3:29])[CH:24]=1)[C:18](OC)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>CCOCC>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:18][OH:19])[CH:22]=[C:23]([CH:25]([CH2:26][NH:27][CH:28]([CH3:29])[CH3:30])[OH:31])[CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 21440626HCID 21440626, compound

Product 1

HCID 86734673HCID 86734673, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of LiAlH4 (4.57 g, 120 moles) in anhydrous Et2O (0.5 l.) was added an ethereal solution (0.5 l.) of the methyl 3-benzyloxy-5-[2(isopropylamino)-1-hydroxyethyl]-benzoate (17.5 g, 50.9 mmoles) slowly at room temperature. The resultant mixture was heated at reflux for 4 hrs. The LiAlH4 and complex was hydrolyzed by the slow addition of 40 ml of H2O. The granular precipitate which formed was removed by filtration and an oily product was obtained from the ether filtrate after evaporation; yield 15.2 g. (94.3%). The crude product was crystallized from Et2O-hexane; yield 9.24 g (54.4%) mp. 84°- 89°. The analytical sample was obtained from EtOAc-hexane, mp. 90°-93° .

Workup

  1. temperatureat reflux for 4 hrs
  2. customThe granular precipitate which formed
  3. customwas removed by filtration
  4. customan oily product was obtained from the ether filtrate
  5. customafter evaporation
  6. customThe crude product was crystallized from Et2O-hexane
  7. customThe analytical sample was obtained from EtOAc-hexane, mp. 90°-93°

Sources & evidence

ORD record
ord-49f23a43a6494458af3be30ad86e2bda
Source dataset
uspto-grants-1977_04
Patent number
US04018825

Reaction notes

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