Hydrochloric Acid → 1-[2-Hydroxy-2-(5-phenyl-1,2-oxazol-3-yl)ethyl]piperidin-4-ol

HRID 1580051Notes

Reaction equation

HRID 1580051 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([C:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:13][N:12]=2)=[O:10])[CH2:4][CH2:3]1.[BH4-].[Na+].Cl>CCOCC.C(O)C>[OH:10][CH:9]([C:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:13][N:12]=1)[CH2:8][N:5]1[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13034601HCID 13034601, compound

Product 1

HCID 30434821-[2-Hydroxy-2-(5-phenyl-1,2-oxazol-3-yl)ethyl]piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(4-hydroxypiperidino)acetyl-5-phenylisoxazole (25 mg) in ether (10 ml) is added a solution of sodium borohydride (15 mg) in ethanol (1.0 ml) with stirring and then the mixture is stirred for 1 hour. After being cooled, the mixture is acidified with a dilute hydrochloric acid and evaporated under reduced pressure. To the residue is added water and the solution is made alkaline with an aqueous solution of potassium hydroxide, then extracted with chloroform. After removal of the solvent, the residue is subjected to a chromatography using silica gel to give crystalline 3-[1-hydroxy-2-(4-hydroxypiperidino) ethyl]-5-phenylisoxazole. Recrystallization from a mixture of ethyl acetate and hexane gives colorless prisms (20 mg) melting at 117-119°C.

Workup

  1. stirringthe mixture is stirred for 1 hour
  2. temperatureAfter being cooled
  3. customevaporated under reduced pressure
  4. additionTo the residue is added water
  5. extractionextracted with chloroform
  6. customAfter removal of the solvent

Sources & evidence

ORD record
ord-7d91a91b6eeb4bf3b0489b36bb5cd174
Source dataset
uspto-grants-1976_01
Patent number
US03932426

Reaction notes

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