Sodium Sulfate → 3-(3,4-Difluorophenyl)-n-methyl-4-amino-1-butanol

HRID 2185908Notes

Reaction equation

HRID 2185908 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH:15]([CH2:19][NH:20][C:21](OCC)=O)[CH2:16][CH2:17][OH:18])[CH:11]=[CH:12][C:13]=1[F:14].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:7][C:8]1[CH:9]=[C:10]([CH:15]([CH2:19][NH:20][CH3:21])[CH2:16][CH2:17][OH:18])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 224526773-(3,4-Difluorophenyl)4-(ethoxycarbonylamino)-1-butanol

Product 1

HCID 224526363-(3,4-Difluorophenyl)-n-methyl-4-amino-1-butanolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred cooled (−10° C.) mixture of lithium aluminum hydride (2.46 g, 65 mmol) and dry THF (50 mL) was added dropwise a solution of 3-(3,4-difluorophenyl)4-(ethoxycarbonylamino)-1-butanol (8.85 g, 32.4 mmol) in THF (40 mL). The solution was heated under reflux for 1.25 h, cooled (ice bath) and saturated sodium sulfate (150 mL) solution was added dropwise. The mixture was stirred at room temperature for 1 hr, filtered through diatomaceous earth, washed with THF and the solvent removed in vacuo. The residue was dissolved in DCM, washed with water, dried (Na2SO4), filtered and the solvent removed in vacuo. Purification by chromatography (2-5% and 10% methanol in DCM) provided the title compound (5.20 g, 75%) as a pale green oil. 1H-NMR (CDCl3) δ 1.85-1.96 (m, 2H, CH) 2.45 (s, 3H, CH3) 2.74-2.85 (m, 3H, CH) 3.37 (br s, 2H, NH, OH) 3.50-3.58 (m, 1H, CH) 3.66-3.73, m, 1H, CH), 6.87-7.35 (m, 3H, ArH). MS m/z 216 (M+H).

Workup

  1. temperatureTo a stirred cooled
  2. temperatureThe solution was heated
  3. temperatureunder reflux for 1.25 h
  4. additionwas added dropwise
  5. filtrationfiltered through diatomaceous earth
  6. washwashed with THF
  7. customthe solvent removed in vacuo
  8. dissolutionThe residue was dissolved in DCM
  9. washwashed with water
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customthe solvent removed in vacuo
  13. customPurification by chromatography (2-5% and 10% methanol in DCM)

Sources & evidence

ORD record
ord-86a05bf519524e949e93c55b4d92a5c1
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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