Benzyl Alcohol → HCID 67223954, compound

HRID 1912408Notes

Reaction equation

HRID 1912408 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:16]([F:20])([F:19])[CH:17]=[CH2:18])(C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.S(=O)(=O)(O)[O-:47].[K+].C([N:54]([CH2:57]C)CC)C>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([NH:54][C:57]([O:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:47])([C:16]([F:19])([F:20])[CH:17]=[CH2:18])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516920Potassium bisulfateHCID 582932793-(1,1-Difluoroallyl)pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

Product 1

HCID 67223954HCID 67223954, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of an optically-active compound of 3-(1,1-difluoroallyl)pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (10.6 g) and triethylamine (10.2 ml) in toluene (106 ml) heated to 100° C. was added dropwise diphenylphosphoryl azide (10.2 ml). The reaction mixture was stirred at 100° C. for 50 minutes, and then thereto were added benzyl alcohol (5.6 ml) and 4-dimethylaminopyridine (0.89 g). The mixture was stirred at 100° C. for 16.5 hours, and then cooled to room temperature. Then, thereto was added 5% aqueous potassium bisulfate solution, and the mixture was extracted with toluene. The organic layer was sequentially washed with 1M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/chloroform/ethyl acetate=5/4/1 to 4/4/1) to give the titled compound (15.5 g).

Workup

  1. stirringThe mixture was stirred at 100° C. for 16.5 hours
  2. temperaturecooled to room temperature
  3. extractionthe mixture was extracted with toluene
  4. washThe organic layer was sequentially washed with 1M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/chloroform/ethyl acetate=5/4/1 to 4/4/1)

Sources & evidence

ORD record
ord-a23d23505dbb4d26990ce93f1b6be37f
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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