Hydrochloric Acid → HCID 12050153, compound

HRID 989805Notes

Reaction equation

HRID 989805 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C@H:6](O)[CH3:7])=[CH:4][CH:3]=1.[N-:11]=[N+:12]=[N-:13].C1CCN2C(=NCCC2)CC1.Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C@@H:6]([N:11]=[N+:12]=[N-:13])[CH3:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33558AzideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 852998(R)-1-(4-Fluorophenyl)ethanol

Product 1

HCID 12050153HCID 12050153, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cooled solution (−15° C.) of the product of Step 1 (23.5 g, 0.168 mol) in toluene (300 ml) was added diphenylphosporyl azide (55.4 g, 0.395 mol) followed by DBU (30.4 ml, 0.2 mol). After stirring overnight, the resulting biphasic solution was poured into 500 ml 1 N HCl. The aqueous layer was extracted with toluene and the combined organic layers were washed with water, 1 N HCl and dried over Na2SO4. After removal of solvent, 25 g of crude product was obtained and was carried on to next step without further purification.

Workup

  1. extractionThe aqueous layer was extracted with toluene
  2. washthe combined organic layers were washed with water, 1 N HCl
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent

Sources & evidence

ORD record
ord-f9c57a16e6744b1d9d26a797e2c84f5c
Source dataset
uspto-grants-2002_10
Patent number
US06458812B1

Reaction notes

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