Water → HCID 117697877, compound

HRID 1778498Notes

Reaction equation

HRID 1778498 reaction equation
[CH2:1]([NH:8][C:9]([CH2:20][CH2:21][CH:22]=[CH2:23])([C:15](OCC)=[O:16])[C:10](OCC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])([O-])(=O)=O.[Na+].[Na+].O>C1COCC1.CCOCC>[CH2:1]([NH:8][C:9]([CH2:20][CH2:21][CH:22]=[CH2:23])([CH2:10][OH:11])[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 117698011HCID 117698011, compound

Product 1

HCID 117697877HCID 117697877, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of diethyl 2-(benzylamino)-2-but-3-enyl-propanedioate 81c (13.9 g, 43.6 mmol) in THF (200 mL) was added standard solution of 2 M LiAlH4 in THF (44 ml) dropwise at ice-bath. The mixture was allowed to warm to room temperature for 3 h. Then the reaction mixture was poured into a mixture of anhydrous sodium sulfate (500 g) and water (50 mL) in ether (300 mL), Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo to afford 2-(benzylamino)-2-but-3-enyl-propane-1,3-diol (9.4 g, 91%) which was used for next step without further purification. MS: calc'd (MH+) 236, measured (MH+) 236.

Workup

  1. filtrationthe insoluble solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8eea6f53da4246d5ad4821848f57bdbc
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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