1-Pentanol → HCID 19857394, compound

HRID 2073569Notes

Reaction equation

HRID 2073569 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.N(C(OC)=O)=NC(OC)=O>O1CCCC1>[CH2:1]([C:35]1[CH:34]=[CH:33][CH:32]=[C:28]2[C:29]([NH:30][C:26](=[O:36])[C:27]=12)=[O:31])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 62761-PentanolHCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl ester

Product 1

HCID 19857394HCID 19857394, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution (60 ml) of 5-(N-tert.butyloxycarbonyl, N-ethylamino)-1-pentanol (4.7 g) in anhydrous tetrahydrofuran were added triphenylphosphine (7.8 g) and phthalimide (4.4 g). To the solution was added dropwise dimethyl azodicarboxylate (5.2 g) with stirring under ice cooling. After stirring was made for one hour, the solvent was distilled off under reduced pressure. The residue was extracted with n-hexane-ethyl acetate (2:1). Solution extracted was washed with water and the solvent was distilled off to obtain N-[5-(N-tert.butyloxycarbonyl, N-ethylamino)] pentylphthalimide (4.2 g).

Workup

  1. stirringAfter stirring
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionThe residue was extracted with n-hexane-ethyl acetate (2:1)
  4. extractionSolution extracted
  5. washwas washed with water
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-42863c6c299d41d4bcd016a4c27cbc9e
Source dataset
uspto-grants-1990_04
Patent number
US04918107

Reaction notes

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