Diethyl Ether → 2-Methylamino-2-phenylbutanol

HRID 1445959Notes

Reaction equation

HRID 1445959 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([NH:9][C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:16][CH3:17])[C:11](OCC)=[O:12])=O.S([O-])([O-])(=O)=O.[Mg+2].C(OCC)C>C1COCC1>[CH3:7][NH:9][C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:16][CH3:17])[CH2:11][OH:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24083Sulfuric acid magnesium salt (1:1)HCID 10633517HCID 10633517, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 107260432-Methylamino-2-phenylbutanolYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 900 mg (23.71 mmol) of lithium aluminum hydride (LiAlH4) in 30 mL of anhydrous THF were added dropwise a solution of 3.09 g (13.15 mmol) of 7, previously prepared, in 18 mL of anhydrous THF. After 4 h under reflux, the reaction mixture was allowed to cool to room temperature and an additional amount of lithium aluminum hydride (900 mg) was introduced. Reflux was maintained for 4 h then an aqueous saturated solution of magnesium sulfate was slowly added at −10° C. under vigorous stirring until formation of a precipitate. The solid was filtered and washed several times with THF. The organic solvent was evaporated under reduced pressure until obtaining of an aqueous solution. The solution was added with 100 mL of diethyl ether and the organic layer was dried over sodium sulfate. Evaporation of the solvent afforded 1.84 g of 8 as a yellow oil. (78% yield).

Workup

  1. temperatureAfter 4 h under reflux
  2. temperatureReflux
  3. temperaturewas maintained for 4 h
  4. filtrationThe solid was filtered
  5. washwashed several times with THF
  6. customThe organic solvent was evaporated under reduced pressure
  7. customuntil obtaining of an aqueous solution
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9826428e6ed9475ca68a0c863db6140b
Source dataset
uspto-grants-2010_02
Patent number
US07666907B2

Reaction notes

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