Tributylstannane → 1-methyl-4-((E)-2-tributylstannanyl-vinyl)-piperidin-4-ol

HRID 1991054Notes

Reaction equation

HRID 1991054 reaction equation
[C:1]([C:3]1([OH:10])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)#[CH:2].[CH3:11][CH2:12][CH2:13][CH2:14][SnH:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][N:6]1[CH2:7][CH2:8][C:3](/[CH:1]=[CH:2]/[Sn:15]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][CH2:12][CH3:11])([OH:10])[CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 14190994-Ethynyl-1-methylpiperidin-4-ol

Product 1

HCID 223495731-methyl-4-((E)-2-tributylstannanyl-vinyl)-piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Ethynyl-1-methylpiperidin-4-ol (Exploratory Library; 3.34 g; 24 mmol) and PdCl2(PPh3)2 (337 mg; 0.48 mmol) were dissolved and stirred in THF (100 ml), cooled in a water bath to 180C, while Bu3SnH (7.6 ml; 28.8 mmol) was added dropwise within 3 minutes. The reaction mixture was stirred at room temperature for 4 hours, poured directly on a column of SiO2 and chromatographed (EtOAc/MeOH/NH3 95/5/0.5) to deliver the title compound as a greenish oil (3.45 g; 33%).

Workup

  1. additionwas added dropwise within 3 minutes
  2. additionpoured directly on a column of SiO2
  3. customchromatographed (EtOAc/MeOH/NH3 95/5/0.5)

Sources & evidence

ORD record
ord-281ec02dabc04fd8be935ca366d9bb6d
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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