1,2,2,6,6-Pentamethyl-4-piperidone → 1,2,2,4,6,6-Hexamethylpiperidin-4-ol

HRID 929994

Reaction equation

HRID 929994 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=[O:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[Li][CH3:14]>C(OCC)C>[CH3:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][C:5]([CH3:14])([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 2419551,2,2,6,6-Pentamethyl-4-piperidoneHCID 178418348HCID 178418348, compound

Product 1

HCID 4345681,2,2,4,6,6-Hexamethylpiperidin-4-olYield 91.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1,2,2,6,6-pentamethylpiperidin-4-one (1.5 g, 8.88 mmol) in diethyl ether (25 mL) at rt was added MeLi (1.6 M, 5.5 mL, 8.88 mmol) slowly. The resulting mixture was stirred at rt for 30 min before it was quenched with sat. NH4Cl (15 mL). The mixture was then partitioned between EtOAc (35 mL) and sat. NaHCO3 (25 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give crude 1,2,2,4,6,6-hexamethylpiperidin-4-ol (1.51 g) as an oil. LC-MS (ESI) m/z 186 (M+H)+.

Workup

  1. customwas quenched with sat. NH4Cl (15 mL)
  2. customThe mixture was then partitioned between EtOAc (35 mL) and sat. NaHCO3 (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea26526e8fa845b3913bf6b5c67a73ea
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Linked notes

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