Tributylstannane → HCID 70214614, compound

HRID 2269368Notes

Reaction equation

HRID 2269368 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13][C:14]#[CH:15])[C:9]1=[O:16].[CH2:17]([SnH:21]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>C1(C)C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13]/[CH:14]=[CH:15]/[Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])[C:9]1=[O:16]

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 20638928HCID 20638928, compound

Product 1

HCID 70214614HCID 70214614, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 1140TolueneSolvent

Procedure

To a solution of (3R,45)-1-(2-tetrahydropyranyloxy)-3-(2-propyne-1-yl)-4-methylazetidin-2-one (1.32 g, 5.83 mmol) in 20 mL of toluene is added tributyltin hydride (1.70 g, 5.83 mmol) and AIBN (30 mg). The resulting solution is heated at reflux for 4 h then concentrated ir vacuo. The reaction mixture is purified by silica gel chromatography (elution with 8:1 hexanes-EtOAc) to provide (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-tributylstannyl-2-propene-1-yl)-4-methylazetidin-2-one as an oil (2.6 g, 87% yield).

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux for 4 h
  3. concentrationthen concentrated ir vacuo
  4. customThe reaction mixture is purified by silica gel chromatography (elution with 8:1 hexanes-EtOAc)

Sources & evidence

ORD record
ord-2465e14c6010465686326c6e6fe83b84
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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