Cyclobutanone → 1-Cyclobutylpiperidin-4-ol

HRID 1523394Notes

Reaction equation

HRID 1523394 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:8]1(=O)[CH2:11][CH2:10][CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)CCl>[CH:8]1([N:1]2[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 79341Piperidin-4-olHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 581554161-Cyclobutylpiperidin-4-olYield 81.46%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-piperidinol (80 g, 0.792 moles) and cyclobutanone (67.2 g, 0.96 moles) in ethylene dichloride (1 L) was treated with sodium triacetoxyborohydride (251.1 g, 1.184 moles) portion wise and the mixture was stirred at room temperature for 5 hours. The reaction mixture was quenched in chilled water (1 L) and the resulting mass was basified with lye solution. The layers were separated, and the aqueous layer was extracted with dichloromethane (2×500 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated to afford the title compound 100 g (Yield: 81.46%).

Workup

  1. customThe reaction mixture was quenched in chilled water (1 L)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (2×500 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53addac1f8e047b0b77bc856c4bc8dde
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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