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

HRID 609545노트

반응식

HRID 609545 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-7d52b3919c5145259226aa4612df7ffd
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998398

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