tert-Butanol → N-1-Boc-Amino-3-cyclopentene

HRID 609545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 609545
[CH:1]1(C(O)=O)[CH2:5][CH:4]=[CH:3][CH2:2]1.C([N:11]([CH2:14]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])C=CC=CC=1.[C:33]([OH:37])([CH3:36])([CH3:35])[CH3:34]>>[CH:1]1([NH:11][C:14](=[O:23])[O:37][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:2][CH:3]=[CH:4][CH2:5]1

Komponenten

5

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 8537563-Cyclopentene-1-carboxylic acid

Produkt 1

HCID 2756764N-1-Boc-Amino-3-cyclopentene

Versuchsvorschrift

To a solution of 3-cyclopentene-1-carboxylic acid (J.-P. Depres and A. E. Greene, J. Org. Chem. 1984, 49:928-931; 29.71 g, 0.261 mole), triethylamine (36.4 mL) in t-butanol (1 L) was added diphenylphosphoryl azide, Aldrich, 97%, 74.0 g, 0.261 mmole). The solution was maintained at 60--C. for 4 hours. Cuprous chloride (1.3 g) was added and stirring continued at ambient temperature for 18 hours. Volatiles were evaporated and the residue was dissolved in methylene chloride (1250 mL) and washed with 10 % aqueous sodium carbonate (2×250 mL) and dried (magnesium sulfate). Volatiles were evaporated and the residue was chromatographed on a silica gel column. Title compound was eluted with chloroform as white crystals, from hexanes (22.63 g, 47%), m.p. 68-70° C.

Aufarbeitung

  1. temperatureThe solution was maintained at 60
  2. waitcontinued at ambient temperature for 18 hours
  3. customVolatiles were evaporated
  4. dissolutionthe residue was dissolved in methylene chloride (1250 mL)
  5. washwashed with 10 % aqueous sodium carbonate (2×250 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customVolatiles were evaporated
  8. customthe residue was chromatographed on a silica gel column
  9. washTitle compound was eluted with chloroform as white crystals, from hexanes (22.63 g, 47%), m.p. 68-70° C.

Quellen und Nachweise

ORD-Eintrag
ord-7d52b3919c5145259226aa4612df7ffd
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998398

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