Tributylstannane → HCID 67260097, compound

HRID 1724627Notes

Reaction equation

HRID 1724627 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@@H:16]([CH2:18]I)[C@@H:14]([OH:15])[C@H:12]1[OH:13].N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@@H:16]([CH3:18])[C@@H:14]([OH:15])[C@H:12]1[OH:13]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 67394619HCID 67394619, compound

Product 1

HCID 67260097HCID 67260097, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1e (80 mg, 0.21 mmol) in anhydrous tetrahydrofuran (12.5 ml) under argon is added 2,2′-azobisisobutyronitrile (AIBN) (38 mg, 0.23 mmol) followed by tributyltin hydride (215 μl, 0.78 mmol). The reaction solution is placed in an 80° C. bath, refluxed 3.5 h, and evaporated to a solid. This material is purified by preparative TLC (Analtech GF, 10×20 cm, 1,000μ) with 9:1 CHCl3/MeOH as solvent. Pure 1f crystallized in two crops from acetonitrile as a white solid.

Workup

  1. customis placed in an 80° C.
  2. temperaturerefluxed 3.5 h
  3. customevaporated to a solid
  4. customThis material is purified by preparative TLC (Analtech GF, 10×20 cm, 1,000μ) with 9:1 CHCl3/MeOH as solvent
  5. customPure 1f crystallized in two crops from acetonitrile as a white solid

Sources & evidence

ORD record
ord-3d81b14c3f33409bbdd0fcd1668309f5
Source dataset
uspto-grants-2009_02
Patent number
US07488598B2

Reaction notes

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