Benzyl Alcohol → HCID 60064125, compound

HRID 412606Notes

Reaction equation

HRID 412606 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19]C(O)=O)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:25]([CH2:28]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.[CH2:47]([OH:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:19][NH:25][C:28]([O:54][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:37])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 60064121HCID 60064121, compound

Product 1

HCID 60064125HCID 60064125, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-tert-butoxycarbonyl-4-ethoxycarbonylpiperidin-4-ylacetic acid (1.6 g) and triethylamine (0.71 ml) in dimethylformamide (20 ml) was added diphenylphosphoryl azide (1.1 ml) at room temperature, and the mixture was stirred at 70° C. for 30 min and then at 90° C. for 10 min. Benzyl alcohol (0.58 ml) was added at the same temperature, and the mixture was stirred for 20 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed with 1N aqueous sodium hydroxide solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography and dried under reduced pressure to give the title compound (1.35 g).

Workup

  1. waitat 90° C. for 10 min
  2. stirringthe mixture was stirred for 20 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with 1N aqueous sodium hydroxide solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by silica gel column chromatography
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-bba84c346eb84037a3ef2bab2d6c7f3d
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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