Sodium hydride → HCID 71293229, compound

HRID 1479293Notes

Reaction equation

HRID 1479293 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(=O)=O.[Cl-].[NH4+]>[Cl-].[Na+].O.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][C@@H:11]([O:13][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C@H:10]([O:14][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7021491(3R,4R)-1-Benzylpyrrolidine-3,4-diolHCID 59753235Linoleyl methanesulfonate

Product 1

HCID 71293229HCID 71293229, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

A toluene (70 mL) solution of (3R,4R)-1-benzylpyrrolidine-3,4-diol (Diverchim S. A.; 3.50 g, 18.1 mmol) was slowly added to a toluene (100 mL) suspension of sodium hydride (oily, 60%, 5.80 g, 145 mmol) while being stirred. A toluene (30 mL) solution of (9Z,12Z)-octadec-9,12-dienyl methanesulfonate (Nu-Chek Prep., Inc.; 15.6 g, 45.3 mmol) was then dropped on the mixture. The resulting mixture was stirred overnight under heat and reflux. After cooling the mixture to room temperature, the reaction was stopped with a saturated ammonium chloride aqueous solution. After adding saturated brine, the mixture was extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/chloroform=0/100 to 2/98) to give compound VI-1 (6.96 g, 55.7%).

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. temperatureunder heat
  3. temperaturereflux
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methanol/chloroform=0/100 to 2/98)
  8. customto give compound VI-1 (6.96 g, 55.7%)

Sources & evidence

ORD record
ord-4201d03f49794589afd52ecb77335198
Source dataset
uspto-grants-2016_08
Patent number
US09408914B2

Reaction notes

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