Sodium Hydroxide → HCID 54519848, compound

HRID 1292640Notes

Reaction equation

HRID 1292640 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][C@@H:4]([CH3:7])[N:3]1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[P:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.[OH-].[Na+]>>[CH3:7][C@@H:4]1[CH2:5][CH2:6][C@@H:2]([CH3:1])[N:3]1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[P:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54523283HCID 54523283, compound

Product 1

HCID 54519848HCID 54519848, compoundYield 26%

Conditions

Temperature
120 °C

Procedure

A two-necked eggplant flask containing 110 mg of 1-((2R,5R)-2,5-dimethylpyrrolidinylmethyl)-2-diphenylphosphinylnaphthalene was purged with nitrogen, and 8 ml of anhydrous xylene was put in and dissolved. Then, 0.22 ml of triethylamine and 0.15 ml of trichlorosilane were added thereto, and the mixture was slowly heated to 120° C. to react for 5 hours. The reaction was ceased with 2N NaOH, and the reaction mixture was extracted with ethyl ether, washed with water, and dried over anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography to obtain 27.1 mg (26%) of the title compound.

Workup

  1. customwas purged with nitrogen, and 8 ml of anhydrous xylene
  2. dissolutiondissolved
  3. additionThen, 0.22 ml of triethylamine and 0.15 ml of trichlorosilane were added
  4. customto react for 5 hours
  5. extractionthe reaction mixture was extracted with ethyl ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d322d2ef074c4ed2b2e793d9fa10e4e5
Source dataset
uspto-grants-1998_05
Patent number
US05756760

Reaction notes

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