Water → HCID 15599314, compound

HRID 1165678Notes

Reaction equation

HRID 1165678 reaction equation
[CH:1](=[N:8][C:9]([CH3:24])([CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[C:10](OCC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH2:1]([NH:8][C:9]([CH3:24])([CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[CH2:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 15599313HCID 15599313, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15599314HCID 15599314, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-benzylideneamino-2-methyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]butyrate (67C, 100.0 g, 0.3 mol) in THF (100 mL) was added slowly to a suspension of lithium aluminum hydride (Morton Thiokol, Inc. -Alfa Products, 22.77 g, 0.6 mol) rapidly stirred in dry THF (1 L) at such a rate to maintain a gentle reflux. After the addition was complete the mixture was refluxed for 4 h. The reaction mixture was cooled and treated successively with H2O (23 mL), 15N NaOH (23 mL) and H2O (45 mL). The solid was removed by filtration and washed with THF (200 mL). The organic layers were combined and concentrated by rotary evaporation to give 2-benzylamino-2-methyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]butanol (81.1 g, 92.0%) as a thick oil which was used without further purification.

Workup

  1. temperatureto maintain a gentle reflux
  2. additionAfter the addition
  3. temperaturewas refluxed for 4 h
  4. temperatureThe reaction mixture was cooled
  5. customThe solid was removed by filtration
  6. washwashed with THF (200 mL)
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-5062663de34c4264841573f0f19ebf2e
Source dataset
uspto-grants-1990_03
Patent number
US04910218

Reaction notes

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