HCID 12851454, compound → HCID 12851455, compound

HRID 1380577Notes

Reaction equation

HRID 1380577 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:30])[CH2:9][CH2:10][C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[C:22]1[C:23]([CH2:28][CH3:29])=[N:24][O:25][C:26]=1[CH3:27])=[O:12]>O1CCCC1>[CH3:30][N:8]([CH3:7])[CH2:9][CH2:10][CH:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[C:22]1[C:23]([CH2:28][CH3:29])=[N:24][O:25][C:26]=1[CH3:27])[OH:12]

Participants

4

Reactant 2

HCID 12851454HCID 12851454, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12851455HCID 12851455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 816 mg. (0.022 mole) of lithium aluminum hydride in 125 ml. tetrahydrofuran under nitrogen is cooled to 5° and treated by dropwise addition with 3.5 g (0.011 mole) of 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone in 125 ml. tetrahydrofuran while maintaining the temperature between 5° to 8° C. The resulting mixture is then stirred for 4 hours at 0° to 5°, then cooled to -50° and quenched by the addition of 10 ml. saturated magnesium sulfate solution. The mixture is warmed to room temperature and filtered and the filtrate is evaporated in vacuo. The resulting residue is dissolved in methylene chloride, washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue is crystallized from ether to give 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanol, m.p. 166°-169° C.

Workup

  1. additionA suspension of 816 mg
  2. temperaturecooled to -50°
  3. customquenched by the addition of 10 ml
  4. filtrationfiltered
  5. customthe filtrate is evaporated in vacuo
  6. dissolutionThe resulting residue is dissolved in methylene chloride
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-fdc4bda050e54df8b718b518981a89d9
Source dataset
uspto-grants-1986_04
Patent number
US04582848

Reaction notes

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