Tributylstannane → 1-Acetyl-4-hydroxy-4-tributylstannyl-piperidine

HRID 1018984Notes

Reaction equation

HRID 1018984 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].[C:26]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=O)(=[O:28])[CH3:27].[O:36]1CCCC1>CCOCC.O>[C:26]([N:29]1[CH2:34][CH2:33][C:32]([OH:36])([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:31][CH2:30]1)(=[O:28])[CH3:27]

Participants

8

Reactant 5

HCID 5948TributylstannaneHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran3×HCID 118159051-Acetylpiperidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 156368991-Acetyl-4-hydroxy-4-tributylstannyl-piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

Under an inert atmosphere, 0.32 mmol of n-butyllithium (1.6M in hexane) is added over a period of 5 minutes to a solution of 0.32 mmol of diisopropylamine in 750 ml of tetrahydrofuran at 0° C. After stirring the mixture for 15 minutes, 0.32 mmol of tri-n-butyltin hydride is added. After 1 hour 30 minutes at 0° C., the reaction mixture is cooled to −70° C. and 0.26 mmol of N-acetylpiperidone in 225 ml of tetrahydrofuran is added and the reaction mixture is then diluted by adding 380 ml of tetrahydrofuran. After stirring for 2 hours 30 minutes, the reaction mixture is hydrolysed by the addition of 200 ml of an aqueous 10% solution of NaH2PO4, brought to 0° C., and then diluted with 2 litres of ether and 1 litre of water. After decanting and washing with a saturated NaCl solution, the organic phase is dried and filtered and then concentrated under reduced pressure. Chromatography on silica gel (dichloromethane) enables the expected product to be isolated.

Workup

  1. waitAfter 1 hour 30 minutes at 0° C.
  2. additionthe reaction mixture is then diluted
  3. stirringAfter stirring for 2 hours 30 minutes
  4. custombrought to 0° C.
  5. customAfter decanting
  6. washwashing with a saturated NaCl solution
  7. customthe organic phase is dried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto be isolated

Sources & evidence

ORD record
ord-5cc0658b833246e3b47e34ddadc15426
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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