Water → HCID 117839768, compound

HRID 1477690Notes

Reaction equation

HRID 1477690 reaction equation
[Br-].[Mg+2].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br-].[CH2:11]([N:18]1[CH2:25][C@H:24]2[C:26](=[O:27])[C@H:20]([CH2:21][O:22][CH2:23]2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.[OH-].[Na+]>C(OCC)(=O)C>[CH2:11]([N:18]1[CH2:19][CH:20]2[C:26]([C:7]3[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=3)([OH:27])[CH:24]([CH2:23][O:22][CH2:21]2)[CH2:25]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 51669033HCID 51669033, compoundHCID 17092348317318-03-5

Product 1

HCID 117839768HCID 117839768, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4-fluorobenzene magnesium bromide (2M diethyl ether solution) (5.0 mL, 10.0 mmol), (1R,5S)-7-benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one (462 mg, 2.00 mmol) was added dropwise at 0° C. and the resultant mixture was stirred at room temperature for 1 minute. After completion of the reaction, water and 1 M sodium hydroxide aqueous solution were added to the reaction solution and extraction from the resultant reaction mixture with ethyl acetate was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel (amino-based) column chromatography (hexane/ethyl acetate=5/1) to obtain the title compound (156 mg, yield 24%).

Workup

  1. additionwere added to the reaction solution and extraction from the resultant
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel (amino-based) column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-35368da11cd1492b8174ced4be7a4be3
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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