Sulfur trioxide-pyridine → HCID 86736984, compound

HRID 1395236Notes

Reaction equation

HRID 1395236 reaction equation
[CH:1]1[CH:6]=[CH:5][N:4]=[CH:3][CH:2]=1.[O:7]=[S:8](=[O:10])=[O:9].[CH3:11][C@@H:12]([C@@H:19]1[C@:36]2([CH3:37])[C:23](=[C:24]3[CH:33]([CH2:34][CH2:35]2)[C@:32]2([CH3:38])[C@H:27]([CH2:28][C@@H:29](O)[CH2:30][CH2:31]2)[CH2:26][CH2:25]3)[C:21](=[O:22])[CH2:20]1)[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17]>C(O)(C)(C)C>[S:8]([O-:22])([O-:10])(=[O:9])=[O:7].[CH3:18][CH:16]([CH2:15][CH2:14][CH2:13][C@H:12]([C@@H:19]1[C@:36]2([CH3:37])[C:23](=[C:24]3[C@H:33]([CH2:34][CH2:35]2)[C@:32]2([CH3:38])[C@H:27]([CH2:28][C@@H:29]([N+:4]4[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=4)[CH2:30][CH2:31]2)[CH2:26][CH2:25]3)[C:21](=[O:22])[CH2:20]1)[CH3:11])[CH3:17].[CH3:18][CH:16]([CH2:15][CH2:14][CH2:13][C@H:12]([C@@H:19]1[C@:36]2([CH3:37])[C:23](=[C:24]3[C@H:33]([CH2:34][CH2:35]2)[C@:32]2([CH3:38])[C@H:27]([CH2:28][C@@H:29]([N+:4]4[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=4)[CH2:30][CH2:31]2)[CH2:26][CH2:25]3)[C:21](=[O:22])[CH2:20]1)[CH3:11])[CH3:17]

Participants

4

Reactant 2

HCID 168533Sulfur trioxide-pyridineHCID 3033012HCID 3033012, compound

Product 1

HCID 86736984HCID 86736984, compoundYield 141%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Pyridine-sulfur trioxide (5.0 g) was added to 5α-cholest-8(14)-en-3β-ol-15-one (2.0 g; 5.0 mmol) in dry chloroform (50 ml; ethanol-free; dried over Linde molecular sieve, type 3A). The resulting mixture was stirred at room temperature for 3 hours. The excess reagent was removed by filtration, washed with a small volume of chloroform, and the filtrate was cooled to -40° C. in a dry ice-acetone bath and filtered through Hyflo Super-Cel (Johns-Manville Corp.). Hexane was added to the chloroform filtrate until a cloudiness appeared whereupon cooling to 0° C. gave a white precipitate. This material was collected by filtration and placed in a vacuum desiccator for 100 hours at room temperature to remove all traces of solvent. The product, 5α-cholest-8(14)-en-15-one-3β-yl pyridinium sulfate (2.4 g; 86% yield), had the following structural formula as confirmed by i.r., n.m.r., and m.s. analyses: ##STR55##

Workup

  1. customThe excess reagent was removed by filtration
  2. washwashed with a small volume of chloroform
  3. temperaturethe filtrate was cooled to -40° C. in a dry ice-acetone bath
  4. filtrationfiltered through Hyflo Super-Cel (Johns-Manville Corp.)
  5. additionHexane was added to the chloroform filtrate until a cloudiness
  6. temperaturewhereupon cooling to 0° C.
  7. customgave a white precipitate
  8. filtrationThis material was collected by filtration
  9. waitplaced in a vacuum desiccator for 100 hours at room temperature
  10. customto remove all traces of solvent

Sources & evidence

ORD record
ord-887b19575214489a93c090ff98cbe4bd
Source dataset
uspto-grants-1980_05
Patent number
US04202891

Reaction notes

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