Sodium borohydride → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxypiperidine

HRID 280893Notes

Reaction equation

HRID 280893 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)=[N:7][O:8][C:4]=2[CH:3]=1.[BH4-].[Na+]>C(O)(C)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH:15]([OH:18])[CH2:16][CH2:17]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 132078191-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone

Product 1

HCID 133198661-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxypiperidineYield 90%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5 g of 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone and 1.4 g of sodium borohydride in 50 ml of isopropanol was stirred at ambient temperature for twenty hrs. The reaction mixture was quenched with methanol and concentrated. The residue was stirred with water and extracted with ether. The organic extracts were washed with water (2x), saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to give 4.5 g (90%) of product. Recrystallization from ether gave the analytical sample, mp 88°-89° C.

Workup

  1. customThe reaction mixture was quenched with methanol
  2. concentrationconcentrated
  3. extractionextracted with ether
  4. washThe organic extracts were washed with water (2x), saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b6de2013ff9d4ef191b957d6120686fc
Source dataset
uspto-grants-1986_05
Patent number
US04591586

Reaction notes

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