Pyridine → HCID 86736632, compound

HRID 1862814Notes

Reaction equation

HRID 1862814 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:8]([CH2:9][OH:10])[CH:7]2[CH2:11][CH:4]1[CH2:5][CH2:6]2.N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O>[S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)([OH:1])(=[O:26])=[O:25].[S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)([OH:1])(=[O:26])=[O:25].[OH:1][CH2:2][C@@H:3]1[C@@H:8]([CH2:9][OH:10])[CH:7]2[CH2:11][CH:4]1[CH2:5][CH2:6]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 57246542HCID 57246542, compound

Product 1

HCID 86736632HCID 86736632, compoundYield 223.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 200 ml round bottom flask capped with a CaCl2 drying tube was placed 7.2 g (0.0461 moles) of (2S,3S)-2,3-bis(hydroxymethyl)bicyclo[2.2.1]heptane (m.p. 58° C.) together with 45 ml of pyridine and 18.4 g (0.096 moles) of p-toluenesulfonyl chloride. The mixture was cooled in an ice bath and stirred for 3 hours and then diluted with 10 ml of H2O. The precipitate which formed was filtered and washed to remove pyridine. The solid was recrystallized from ethanol to give 17.2 g (92%) of fine white needles, m.p. 100-101° C., αD =+32.2° C.

Workup

  1. customIn a 200 ml round bottom flask capped with a CaCl2 drying tube
  2. temperatureThe mixture was cooled in an ice bath
  3. customThe precipitate which formed
  4. filtrationwas filtered
  5. washwashed
  6. customto remove pyridine
  7. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-622d31c5d6f944acab13419af98f22fa
Source dataset
uspto-grants-1979_09
Patent number
US04166824

Reaction notes

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