Tetrahydrofuran → HCID 12072836, compound

HRID 1356557Notes

Reaction equation

HRID 1356557 reaction equation
O1CCCC1.[C:6]([O:10][C:11]([NH:13][C@:14]12[CH2:22][CH:21]1[CH2:20][C@H:19]1[C@@H:15]2[CH2:16][N:17]([C:23](=O)[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH2:18]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[OH-].[Na+]>O>[C:6]([O:10][C:11]([NH:13][C@:14]12[CH2:22][CH:21]1[CH2:20][C@H:19]1[C@@H:15]2[CH2:16][N:17]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[CH2:18]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12072835HCID 12072835, compound

Product 1

HCID 12072836HCID 12072836, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1M tetrahydrofuran solution (7.0 ml) of a borane-tetrahydrofuran complex (7.0 mmol) was added dropwise to a tetrahydrofuran (20 ml) solution of (1R,2R,6S)-1-t-butoxycarbonylamino-4-p-anisoyl-4-azatricyclo[6.1.0.02,6]nonane (970 ml, 2.60 mmol) while cooling with ice, and the mixture was stirred at room temperature for 1 hour. While cooling with ice, water was added to the reaction mixture to decompose the excess borane-tetrahydrofuran complex. A 1N sodium hydroxide aqueous solution (10 ml) was added thereto, followed by refluxing for 6 hours. After cooling to room temperature, the reaction mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 453 mg (1.26 mmol, 48%) of the title compound as a colorless oily substance.

Workup

  1. temperaturewhile cooling with ice
  2. additionwas added to the reaction mixture
  3. temperatureby refluxing for 6 hours
  4. temperatureAfter cooling to room temperature
  5. extractionthe reaction mixture was extracted with diethyl ether
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-6824cd6418dc43edb7d07c8910070c08
Source dataset
uspto-grants-2003_07
Patent number
US06586604B2

Reaction notes

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