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

HRID 609545ノート

反応式

HRID 609545 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-7d52b3919c5145259226aa4612df7ffd
出典データセット
uspto-grants-1999_12
特許番号
US05998398

反応ノート

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