Sodium Sulfate → HCID 11487279, compound

HRID 2293341Notes

Reaction equation

HRID 2293341 reaction equation
[CH:1]([N:4]([CH2:8][CH2:9][CH:10]([C:17]1[CH:22]=[C:21]([C:23](OC)=[O:24])[CH:20]=[CH:19][C:18]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.O>[CH:1]([N:4]([CH2:8][CH2:9][CH:10]([C:17]1[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[CH:19][C:18]=1[O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:5]([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 166653HydrideHCID 9804258Methyl 4-(benzyloxy)-3-(3-(diisopropylaMino)-1-phenylpropyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11487279HCID 11487279, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

(+)-N,N-Diisopropyl-3-(2-benzyloxy-5-carbomethoxyphenyl)-3-phenylpropylamine (30 g, 0.065 mole) dissolved in diethyl ether (250 mL) was added dropwise under nitrogen to a suspension of lithium aluminiumhydride (1.9 g, 0.05 mole) in dry diethyl ether (150 mL). The mixture was stirred overnight at room temperature, and the excess hydride was decomposed by the addition of water (≈5 g). The mixture was stirred for 10 min, when sodium sulfate (s) was added. After stirring for 20 minutes, the mixture was filtered and then evaporated to give 28.4 g of the title compound as a colourless oil.

Workup

  1. stirringThe mixture was stirred for 10 min
  2. stirringAfter stirring for 20 minutes
  3. filtrationthe mixture was filtered
  4. customevaporated

Sources & evidence

ORD record
ord-9567792df69e49eaa808db65d0c21547
Source dataset
uspto-grants-1997_11
Patent number
US05686464

Reaction notes

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