Water → 4-Piperidinemethanol, 1-benzoyl-

HRID 1291195Notes

Reaction equation

HRID 1291195 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15](OCC)=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B([O-])([O-])[O-].[Li+].[Li+].[Li+].B(OC)(OC)OC.O>C1COCC1>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8470Trimethyl borateHCID 735824Ethyl 1-benzoylpiperidine-4-carboxylateHCID 13743157Trilithium borate

Product 1

HCID 102628704-Piperidinemethanol, 1-benzoyl-Yield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.4 g (0.04 mol) of ethyl 1-benzoyl-4-piperidine-carboxylate were dissolved in 90 ml of THF and treated with a solution of 0.871 g (0.04 mol) of lithium borate in 20 ml of THF. 0.45 ml (0.004 mol) of trimethyl borate was added and the mixture was stirred at room temperature for 60 hrs. The reaction mixture was treated with water and stirred for 1.5 hrs. The mixture was extracted with ethyl acetate and the organic phase was washed with water and saturated sodium chloride solution and dried over sodium sulfate. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:1). 7.8 g (90%) of 1-benzoyl-4-hydroxymethyl-piperidine were obtained as white crystals; m.p. 84°-87°.

Workup

  1. stirringstirred for 1.5 hrs
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-7f6c9900f2484e1da42ec8aeb541153a
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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