Tetrabutylammonium Fluoride → Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylate

HRID 2172987Notes

Reaction equation

HRID 2172987 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:32][C@H:31](OS(C)(=O)=O)[C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1.O>[C:19]([O:23][C:24]([NH:26][C@@:27]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH:32]=[CH:31][C@@H:30]2[C@H:28]1[C@H:29]2[C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86695971HCID 86695971, compound

Product 1

HCID 71681345Di-tert-butyl (1S,2S,5R,6S)-2-[(tert-butoxycarbonyl)amino]bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add 1M tetrabutylammonium fluoride in tetrahydrofuran (3.84 mL, 3.84 mmol) to di-tert-butyl (1S,2S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (600.00 mg, 1.22 mmol) in tetrahydrofuran (2.03 mL) and heat at reflux for 3 hours. The reaction is then cooled to room temperature, diluted with water, and extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography eluting with 5-75% ethyl acetate in hexanes to give the title compound (0.23 g, 0.58 mmol, 48%).

Workup

  1. temperatureheat
  2. temperatureat reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. customThe residue is purified by flash chromatography
  10. washeluting with 5-75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f31df39bb429447aaeab2ee101695153
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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