Sodium borohydride → 1-Methoxypiperidin-4-ol

HRID 1473783Notes

Reaction equation

HRID 1473783 reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 199366531-Methoxypiperidin-4-one

Product 1

HCID 30226061-Methoxypiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-methoxy-piperidin-4-one [prepared according to Journal of Organic Chemistry (1961), 26, 1867-74] (15.0 g, 116.1 mmol) in ethanol (430 ml) was added sodium borohydride 96% (2.29 g, 58.1 mmol) in portions. The reaction mixture was stirred at room temperature for 5 hours, evaporated to half of its volume, poured on cold saturated aqueous ammonium chloride and thoroughly extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate). Yield: 10.9 g of 1-methoxy-piperidin-4-ol as a liquid.

Workup

  1. customevaporated to half of its volume
  2. additionpoured on cold saturated aqueous ammonium chloride
  3. extractionthoroughly extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-68199146adf349e895f22e1e5de378d0
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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