Sulfuric Acid → HCID 67459717, compound

HRID 554554Notes

Reaction equation

HRID 554554 reaction equation
[BH4-].[Na+].[CH:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[O:20][C@@H:21]3[CH2:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@@H:24]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@H:23]([O:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C@H:22]3[O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[O:13])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1COCC1.O>[CH:3]1([C:6]2[CH:7]=[CH:8][C:9]([CH:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[O:20][C@@H:21]3[CH2:26][C@H:25]([CH2:27][O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@@H:24]([O:36][CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C@H:23]([O:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C@H:22]3[O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[OH:13])=[CH:10][CH:11]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 67460302HCID 67460302, compound

Product 1

HCID 67459717HCID 67459717, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium borohydride (40 mg, 1.06 mmol) was added to a solution of (4-cyclo-propylphenyl)-[3-((1R,2S,3S,4R,5R)-2,3,4-trisbenzyloxy-5-benzyloxymethylcyclohexyloxy)pyridin-4-yl]methanone (0.20 g, 0.26 mmol) in THF (1.37 mL) and water (0.67 mL) under cooling with ice and the reaction mixture was stirred at room temperature for 14.5 hours. To the reaction mixture, THF was added, and concentrated sulfuric acid (0.2 mL) was added thereto under cooling with ice and the reaction mixture was stirred for 10 minutes. To the obtained reaction mixture was added a saturated sodium hydrogencarbonate aqueous solution and the mixture was stirred at room temperature for 10 minutes. The resulting mixture was extracted with ethyl acetate and the organic layer was dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (3:2)] to obtain the title product (0.20 g, 100%) as a diastereomeric mixture.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe reaction mixture was stirred for 10 minutes
  4. customTo the obtained reaction mixture
  5. stirringthe mixture was stirred at room temperature for 10 minutes
  6. extractionThe resulting mixture was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried (anhydrous magnesium sulfate)
  8. distillationthe solvent was distilled under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (3:2)]

Sources & evidence

ORD record
ord-52500e8db1554278b89932b08e0c9a43
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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