Tributylstannane → HCID 71007967, compound

HRID 2361711Notes

Reaction equation

HRID 2361711 reaction equation
I[CH:2]1[CH2:10][CH:9]2[CH2:11][C:5]3([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:7]([CH2:12][CH:3]1[CH2:4]3)[CH2:8]2.CC(N=NC(C#N)(C)C)(C#N)C.CCCC[SnH](CCCC)CCCC>C1(C)C=CC=CC=1>[C:5]12([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:11][CH:9]3[CH2:8][CH:7]([CH2:12][CH:3]([CH2:2][CH2:10]3)[CH2:4]1)[CH2:6]2

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86673700HCID 86673700, compound

Product 1

HCID 71007967HCID 71007967, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of iodide 5A (0.18 mmol), AIBN (0.054 mmol), and Bu3SnH (0.54 mmol) was diluted with toluene (10 mL) and the reaction mixture was heated at 90° C. for 2 h. The reaction mixture was concentrated and the residue was purified by silica gel chromatography (10/90 EtOAc/Hexane) to provide the reduction product 6A in 73% yield. Data: LC/MS (ESR) m/z 266 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel chromatography (10/90 EtOAc/Hexane)

Sources & evidence

ORD record
ord-1e80158e729748a8a3b9958b9ae0c0df
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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