Sodium borohydride → [3-(3-Piperidin-1-yl-propoxy)-isoxazol-5-yl]-methanol

HRID 30485Notes

Reaction equation

HRID 30485 reaction equation
C[O:2][C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=1)=O.[BH4-].[Na+]>CCO>[N:14]1([CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[O:9][N:8]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 445154593-(3-Piperidin-1-yl-propoxy)-isoxazole-5-carboxylic acid methyl ester

Product 1

HCID 44515460[3-(3-Piperidin-1-yl-propoxy)-isoxazol-5-yl]-methanolYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3-piperidin-1-yl-propoxy)-isoxazole-5-carboxylic acid methyl ester (0.200 g, 0.750 mmol) in EtOH (15 mL) was added NaBH4 (0.358 g, 11.2 mmol) was slowly over 30 min. The reaction mixture was heated at reflux overnight, then was cooled to rt and quenched by the addition of 1 N NaOH (10 mL). The mixture was stirred for 1 h, and then was extracted with DCM (3×30 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to yield the desired alcohol (0.177 g, 99%). MS (ESI): exact mass calcd. for C12H20N2O3, 240.15; m/z found, 241.3 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customquenched by the addition of 1 N NaOH (10 mL)
  4. extractionwas extracted with DCM (3×30 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4fb12e859a844246a266bae6761ac7a9
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Reaction notes

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