Sodium hydride → HCID 58348375, compound

HRID 2192309Notes

Reaction equation

HRID 2192309 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[N:18]12CC[CH:21]([CH2:22][CH2:23]1)[C@@H:20](O)[CH2:19]2.[H-].[Na+]>C1(C)C=CC=CC=1>[N:18]12[CH2:23][CH2:22][CH:21]([CH2:20][CH2:19]1)[C@@H:1]([O:3][C:4]([C:6]1([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH2:2]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 914043-Quinuclidinol, (-)-HCID 583483241-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl ester

Product 1

HCID 58348375HCID 58348375, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl ester (Example 5c) (2.5 g) and (R) -quinuclidin-3-ol (2.08 g) were dissolved in toluene (350 mL) and sodium hydride (0.1 g) added under nitrogen. The mixture was heated to reflux for 20 hours after which the toluene was carefully distilled off to leave ˜100 mL which was cooled and washed with water (100 mL), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica eluting with ethyl acetate/triethylamine (99/1) to afford the sub-titled compound (2.84 g).

Workup

  1. temperatureThe mixture was heated
  2. distillationwas carefully distilled off
  3. customto leave ˜100 mL which
  4. temperaturewas cooled
  5. washwashed with water (100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica eluting with ethyl acetate/triethylamine (99/1)

Sources & evidence

ORD record
ord-fe6cd7a005eb407dada9857f460b8b7b
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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