Tributyltin Chloride → HCID 67002664, compound

HRID 2362729Notes

Reaction equation

HRID 2362729 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]12[CH2:13][N:10]([CH2:11][CH2:12]1)[CH2:9][CH2:8][O:7]2.C([N-]C(C)C)(C)C.[Li+].[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>O1CCCC1>[CH2:31]([Sn:26]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:27][CH2:28][CH2:29][CH3:30])[C:5]1[S:1][C:2]([C:6]23[CH2:13][N:10]([CH2:11][CH2:12]2)[CH2:9][CH2:8][O:7]3)=[N:3][CH:4]=1)[CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 2724682Lithium diisopropylamideHCID 58513737HCID 58513737, compound

Product 1

HCID 67002664HCID 67002664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of the 5-(thiazol-2-yl)-4-oxa-1-azabicyclo[3.2.1]octane (632 mg, 3.22 mmol) in tetrahydrofuran (11 mL) was added a solution of lithium diisopropylamide (7.79 mmol in 10 mL tetrahydrofuran) dropwise. The solution was stirred at −78° C. for 45 minutes, and tributyltin chloride (1.05 mL, 3.86 mmol) was added dropwise. The cold bath was removed, and the reaction allowed to warm to room temperature. The ambient reaction was then quenched by the addition of saturated aqueous ammonium chloride solution and diethyl ether. The layers were separated, and the aqueous layer was extracted with additional diethyl ether. The combined organics were washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 487.4 [M+H]+.

Workup

  1. customThe cold bath was removed
  2. temperatureto warm to room temperature
  3. customThe ambient reaction
  4. customwas then quenched by the addition of saturated aqueous ammonium chloride solution and diethyl ether
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with additional diethyl ether
  7. washThe combined organics were washed with water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10128de2fa114340aa67ce4cbc638e61
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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