Tributyltin Chloride → HCID 58266640, compound

HRID 1888465Notes

Reaction equation

HRID 1888465 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C([Li])CCC.[CH2:18]([Sn:22](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21].C(=O)([O-])O.[Na+]>C1COCC1>[CH2:27]([Sn:22]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:23][CH2:24][CH2:25][CH3:26])[C:5]1[S:1][C:2]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)=[N:3][CH:4]=1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 23055008HCID 23055008, compoundHCID 178418339Butyllithium

Product 1

HCID 58266640HCID 58266640, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−78° C.) solution of 1-thiazol-2-ylmethylpiperidine (2.73 g, 15.0 mmol) anhydrous THF (100 mL) was added n-butyllithium (8.95 mL, 16.5 mmol). After 30 minutes, a solution of tributyltin chloride (4.93 mL, 18.2 mmol) in anhydrous THF (40 mL) was to the reaction mixture. After 10 minutes, the solution was allowed to warm to ambient temperature and saturated aqueous sodium hydrogen carbonate was added. The aqueous phase was extracted with tert-butylmethyl ether (3×50 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a colourless oil that was then purified by flash chromatography (silica, 12 g column, ISCO, 0-40% ethyl acetate in cyclohexane) to afford the title compound as a colourless oil (5.1 g, 72%). 1H NMR (CDCl3, 400 MHz): 7.62 (t, J=6.4 Hz, 1H), 3.88 (s, 2H), 2.54-2.47 (m, 4H), 1.69-1.49 (m, 10H), 1.50-1.40 (m, 2H), 1.40-1.26 (m, 6H), 1.15-1.08 (m, 6H), 0.95-0.85 (m, 9H).

Workup

  1. waitAfter 10 minutes
  2. extractionThe aqueous phase was extracted with tert-butylmethyl ether (3×50 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a colourless oil that
  7. customwas then purified by flash chromatography (silica, 12 g column, ISCO, 0-40% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-3a407445c5814a748e95d26c12896baa
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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