Cyclobutanone → 1-Cyclobutylpiperidin-4-ol

HRID 1696697Notes

Reaction equation

HRID 1696697 reaction equation
C([BH3-])#N.[Na+].[OH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:12]1(=O)[CH2:15][CH2:14][CH2:13]1>CO>[CH:12]1([N:9]2[CH2:10][CH2:11][CH:6]([OH:5])[CH2:7][CH2:8]2)[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 79341Piperidin-4-olHCID 5003444Sodium cyanoborohydride

Product 1

HCID 581554161-Cyclobutylpiperidin-4-olYield 1,082.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol solution (48 mL) of 0.3 N sodium cyanoborohydride/0.15 N zinc(II) chloride was added to a methanol (50 mL) solution of 4-hydroxypiperidine (1.1 g, 1.0 mmol) and cyclobutanone (1 g), and stirred at room temperature for 24 hours. The solvent was concentrated under reduced pressure, distilled water was added, and extracted eight times with chloroform. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure to obtain the entitled compound (1.68 g, 98%) as a yellow oil.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. distillationdistilled water
  3. additionwas added
  4. extractionextracted eight times with chloroform
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c34d0e0b621940438de3811a82352c99
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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