Water → HCID 18998802, compound

HRID 2260645Notes

Reaction equation

HRID 2260645 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:17](O)=[O:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:27]=[CH:26][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:17][OH:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 18998812HCID 18998812, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18998802HCID 18998802, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 3-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino)-2-phenylpropanoic acid (1.8 g, 5 mmol) in 25 ml dry toluene, stirred at 0° C., a solution of LiAlH4 in THF (5 ml, 1M, 5 mmol) was added dropwise. 20 min. after addition was completed the mixture was allowed to warm to room temperature for 15 min. whereupon H2O was added dropwise to precipitate aluminum hydroxide. To the organic phase was added 50 ml ether, and the mixture was washed with water and concentrated in vacuo to get 1.6 g of 3-(4-(6-fluoro -1,2-benzisoxazol-3-yl)piperidino)-2-phenylpropanol as an oil.

Workup

  1. addition20 min. after addition
  2. additionwas added dropwise
  3. customto precipitate aluminum hydroxide
  4. additionTo the organic phase was added 50 ml ether
  5. washthe mixture was washed with water
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8901eeff8b4b4ec9b0eff113e1b364b6
Source dataset
uspto-grants-1995_12
Patent number
US05478845

Reaction notes

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