Tributylstannane → HCID 71183690, compound

HRID 2274156Notes

Reaction equation

HRID 2274156 reaction equation
C([SnH](CCCC)CCCC)CCC.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[CH:23](OC(N1C=CN=C1)=S)[CH:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1>C1C=CC=CC=1>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 86675575HCID 86675575, compound

Product 1

HCID 71183690HCID 71183690, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.15 g (4.36 mmol) of tributyltin hydride, 53.71 mg (0.33 mmol) of α,α′-azoisobutyronitrile and 1.0 g (2.18 mmol) of tert-butyl 3-[benzothiazol-2-yl(imidazole-1-carbothioyloxy)methyl]-piperidine-1-carboxylate were dissolved successively in 10 ml of benzene at room temperature. After 2 min with stirring, a vacuum was applied, and the mixture was degassed for 2 min. This operation was repeated. The reaction mixture was subsequently stirred under reflux for 45 min. Conventional work-up gave 0.58 g of tert-butyl 3-benzothiazol-2-ylmethylpiperidine-1-carboxylate; HPLC/MS (M+H)+=333 as oil.

Workup

  1. customthe mixture was degassed for 2 min
  2. stirringThe reaction mixture was subsequently stirred
  3. temperatureunder reflux for 45 min

Sources & evidence

ORD record
ord-08d5d7cf30e2432894d8992c2a248040
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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