Iodine → 3-Methyl-5-(1-CBZ-2(S)-pyrrolidinyl)isoxazole

HRID 21771Notes

Reaction equation

HRID 21771 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=[CH:17][C:18](=[N:20][OH:21])[CH3:19])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([O-])(O)=O.[Na+].II>O.OS([O-])=O.[Na+]>[C:1]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[O:21][N:20]=[C:18]([CH3:19])[CH:17]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 852958861-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one oxime

Product 1

HCID 109460703-Methyl-5-(1-CBZ-2(S)-pyrrolidinyl)isoxazoleYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 23665763Sodium BisulfiteSolvent

Procedure

To a stirred solution of 6 g (20.83 mmol) of the oxime compound from step 24f above, in a wrapped flask to protect from light, was added 12.1 g (72.92 mmol) of Kl dissolved in 80 mL of water and, in small portions, 7 g (83.33 mmol) of NaHCO3 and 15.86 g (62.5 mmol) of iodine. The reaction was heated at reflux for 16 hr, cooled and diluted with saturated aq. NaHSO3. The solution was extracted with ether, and the extract was washed with saturated aq. NaHSO3, dried over Na2SO4, and concentrated to afford the title product (5.06 g, 85% yield). The compound was taken to the next step without further purification. IR 1702, 1604, 1444, 1417, 1356, 1173, 1103, 1079 cm-1.

Workup

  1. additionwas added 12.1 g (72.92 mmol) of Kl
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 16 hr
  4. temperaturecooled
  5. extractionThe solution was extracted with ether
  6. washthe extract was washed with saturated aq. NaHSO3
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4223c27f3a474aa3bce86f4853684e93
Source dataset
uspto-grants-1995_06
Patent number
US05424444

Reaction notes

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