Ethyl 1-benzoylpiperidine-4-carboxylate → 4-Piperidinemethanol, 1-benzoyl-

HRID 1681182Notes

Reaction equation

HRID 1681182 reaction equation
[BH4-].[Li+].[C:3]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](OCC)=[O:18])[CH2:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[C:3]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 735824Ethyl 1-benzoylpiperidine-4-carboxylateHCID 4148881Lithium borohydride

Product 1

HCID 102628704-Piperidinemethanol, 1-benzoyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium borohydride in tetrahydrofuran (2 M, 0.95 mL, 1.9 mmol) was added dropwise to a solution of ethyl 1-benzoylpiperidine-4-carboxylate (1 g, 3.8 mmol) in tetrahydrofuran (10 mL) with stirring under a nitrogen atmosphere. The reaction mixture was stirred for 18 h, poured onto water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography (ethylacetate) afforded 1-benzoyl-4-hydroxymethylpiperidine, a solid (522 mg, Rf =0.14): m.p. 85°-87° C.; 'H-NMR (CDCl3, 200 MHz): 7.45-7.35 (m, 5H), 4.8-4.6 (m, 1H), 3.9-3.7 (m, 1H), 3.5 (br s, 2H), 3.2-3.6 (m, 3H), 2.25 (br s, 1H), 2.0-1.6 (m, 3H), 1.4-1.0 (m, 2H); HRMS: Calcd. for C13H17NO2 :219.1259; Found: 19.1245.

Workup

  1. stirringThe reaction mixture was stirred for 18 h
  2. additionpoured onto water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23bba6ecea794d8384724ca431ddf167
Source dataset
uspto-grants-1992_12
Patent number
US05169855

Reaction notes

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