Triethylamine → 1-[4-(Tributylstannyl)-3,6-dihydropyridin-1(2H)-yl]ethan-1-one

HRID 2166496Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][C:7](O)([Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:5][CH:6]=[C:7]([Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1-Acetyl-4-hydroxy-4-tributylstannyl-piperidine, 20 (16.4 g, 38 mmol) and triethylamine (15.0 ml, 108 mmol) were dissolved in methylene chloride (250 ml) and the solution cooled to 0° C. Methanesulfonylchloride (6.0 ml, 50 mmol) in methylene chloride (50 ml) was added dropwise to the cooled solution and the mixture was allowed to warm to room temperature and stir for 60 hours. The reaction solution was washed with NaCl solution, dried (MgSO4), filtered, and evaporated to give a red oil which was purified by flash column chromatography on silica gel, eluting with 3% ethanol in CH2Cl2. After combining the appropriate fractions and evaporating the solvent, the title compound, 21, was obtained (7.5 g).

Workup

temperatureto warm to room temperature
washThe reaction solution was washed with NaCl solution
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customto give a red oil which
customwas purified by flash column chromatography on silica gel
washeluting with 3% ethanol in CH2Cl2
customevaporating the solvent

Sources & evidence

ORD record: ord-e7279b2515a4451cac7ec3db49515000
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04945160

Reaction notes

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