Tributylstannane → HCID 67979307, compound

HRID 528758Notes

Reaction equation

HRID 528758 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12](SC)(OC(O)=S)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[SnH](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 178504076HCID 178504076, compound

Product 1

HCID 67979307HCID 67979307, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To 428 mg (1.21 mmol) 3-(methylsulfanylthiocarboxyoxy-pyridin-2-yl-methyl)-azetidine-1-carboxylic acid tert-butyl ester in 15 mL dry toluene was added 6 mg (36 μmol) AlBN followed by 508 mg (1.69 mmol) nBu3SnH, and the mixture was heated under nitrogen at 110° C. for 2 hours. After evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 1:1 to EtOAc).

Workup

  1. customAfter evaporation of the solvent the product
  2. customwas purified by column chromatography (silica, heptane/EtOAc 1:1 to EtOAc)

Sources & evidence

ORD record
ord-26f9a65e85c94916afbcec502c4405f8
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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