1-Iodopropane → propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate

HRID 1196644Notes

Reaction equation

HRID 1196644 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].[C:26]1([C:37]2CCCCCCCCCC=2)[CH2:36]CCCCCCCNN=1.C(I)CC>CC(C)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH:26]([CH3:37])[CH3:36])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 5280363DinoprostHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 5283077propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20 mg (0,056 mmol) of 11 epi PGF2alpha (Cayman Chemicals, U.S.) were dissolved in acetone at room temperature. To this solution were added 54.5 mg (0.336 mmol) of diazabicycloundecene (DBu) and 76.15 mg (0.448 mmol) of propyl iodide, whereupon the mixture was left to stand at room temperature for 8 hours. The solvent was removed in vacuo, the residue then being dissolved in 50 ml of ethyl acetate, washed with 20 ml of water, 20 ml of 3% citric acid and 5% sodium hydrogen carbonate; thereafter the organic phase was dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by means of column chromatography on silica gel, with ethyl acetate-acetone (1:1) as the eluent. The yield of the product was about 76%, and its purity was tested by means of thin layer chromatography and NMR.

Workup

  1. waitwhereupon the mixture was left
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue then being dissolved in 50 ml of ethyl acetate
  4. washwashed with 20 ml of water, 20 ml of 3% citric acid and 5% sodium hydrogen carbonate
  5. dry with materialthereafter the organic phase was dried over sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by means of column chromatography on silica gel, with ethyl acetate-acetone (1:1) as the eluent

Sources & evidence

ORD record
ord-202edb9b4ca7480f8a5dae1e93c7b22b
Source dataset
uspto-grants-1992_05
Patent number
US05114971

Reaction notes

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