Benzyl Alcohol → HCID 67428133, compound

HRID 1662053Notes

Reaction equation

HRID 1662053 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1(C(O)=O)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1(P([N:32]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[H-].[Na+].C([O:48][CH2:49]C)(=O)C>O.CN(C=O)C.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH2:35]([O:42][C:49]([NH:32][C:9]1([CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13]1)=[O:48])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

10

Reactant 5

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 199401P,P-Diphenylphosphinic azideHCID 11010130t-Butyl 3-(1-carboxycyclopentyl)propanoate

Product 1

HCID 67428133HCID 67428133, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 1-(3-tert-butoxy-3-oxopropyl)cyclopentanecarboxylic acid (0.95 g) and toluene (10 ml) were added triethylamine (0.48 g), and diphenylphosphoryl azide (1.2 g) under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was stirred at 100° C. for 0.5 hour, and then stirred under ice-cooling to give a mixture A. Apart from this, a mixture of DMF (2.0 ml) and benzyl alcohol (0.45 ml) was stirred at room temperature, and sodium hydride (0.18 g) was added thereto, followed by stirring for 0.5 hour to give a mixture B. Next, to the mixture A was added the mixture B under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture were added ethyl acetate and water, and the aqueous layer was separated and extracted with ethyl acetate. The organic layer was combined, washed with a 10% aqueous citric acid solution, a saturated sodium bicarbonate solution, water, and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain tert-butyl 3-(1-{[(benzyloxy)carbonyl]amino}cyclopentyl)propanoate (0.59 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at 100° C. for 0.5 hour
  3. stirringstirred under ice-
  4. temperaturecooling
  5. customto give a mixture A
  6. stirringwas stirred at room temperature
  7. stirringby stirring for 0.5 hour
  8. customto give a mixture B
  9. additionNext, to the mixture A was added the mixture B under ice-
  10. temperaturecooling
  11. stirringby stirring at room temperature for 1 hour
  12. customthe aqueous layer was separated
  13. extractionextracted with ethyl acetate
  14. washwashed with a 10% aqueous citric acid solution
  15. dry with materiala saturated sodium bicarbonate solution, water, and saturated brine in this order, dried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-067b78a8ef784519a6f2a2a90caca407
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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