Sodium Hydroxide → 57962-58-0

HRID 1353178Notes

Reaction equation

HRID 1353178 reaction equation
[Br-].C([N+]1N=C([C@@H](OC)C)N([NH:18][CH:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]([O:23][CH3:24])[O:21][CH3:22])C=1[C@@H](OC)C)C1C=CC=CC=1.[BH4-].[Li+].[OH-].[Na+]>O1CCCC1>[C:25]1([CH:19]([NH2:18])[CH:20]([O:23][CH3:24])[O:21][CH3:22])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 21102633HCID 21102633, compound

Product 1

HCID 2171402757962-58-0Yield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6 ml of tetrahydrofuran (THF) and 3.5 mmol of 1-benzyl-4-(1-phenyl-2,2-dimethoxyethylamino)-(S,S)-3,5-bis(1-methoxyethyl)-1,2,4-triazolium bromide are introduced into a 100 ml round-bottomed flask equipped with a reflux condenser and a magnetic stirrer and then 1.75 ml of a 2 mol/l solution of lithium borohydride in THF are added at ambient temperature over a period of 1 to 2 h approximately. The reaction medium is subsequently left stirring at ambient temperature for 3 h and then brought to reflux for 3 h. After returning to ambient temperature, 20 ml of a 20% aqueous sodium hydroxide solution are added and then the aqueous phase is extracted with dichloromethane. The resulting organic phase is dried over anhydrous magnesium sulphate and then concentrated. The amine is purified by distillation. 0.19 g of the expected compound is obtained.

Workup

  1. customequipped with a reflux condenser and a magnetic stirrer
  2. waitThe reaction medium is subsequently left
  3. temperatureto reflux for 3 h
  4. customAfter returning to ambient temperature
  5. extractionthe aqueous phase is extracted with dichloromethane
  6. dry with materialThe resulting organic phase is dried over anhydrous magnesium sulphate
  7. concentrationconcentrated
  8. distillationThe amine is purified by distillation

Sources & evidence

ORD record
ord-bcec862df84447dc855c4ed33cf0446c
Source dataset
uspto-grants-2007_05
Patent number
US07220883B2

Reaction notes

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