Triacetoxyperiodinane → HCID 57659763, compound

HRID 1011602Notes

Reaction equation

HRID 1011602 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][CH:12]([CH:14]2[CH2:16][CH2:15]2)[N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:10]1[CH:24]1[CH2:26][CH2:25]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1>[CH:24]1([C@H:10]2[C:9](=[O:8])[CH2:13][CH:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 2724141Tetrabutylammonium FluorideHCID 67313638HCID 67313638, compound

Product 1

HCID 57659763HCID 57659763, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,3R)-tert-Butyl 3-(tert-butyldimethylsilyloxy)-2,5-dicyclopropylpyrrolidine-1-carboxylate (19) (412 mg, 1.08 mmol) was dissolved in THF (1 mL) and placed under nitrogen. TBAF (IM THF, 1.29 mL) was added and the reaction stirred for 2 hr. The reaction was concentrated in vacuo and used without further purification. This material was dissolved in CH2Cl2 (2 mL) and placed under nitrogen. Dess-Martin reagent (788 mg, 1.86 mmol) was added and the reaction quenched with sat. aq. NaHCO3 (2 mL) followed by sat. Na2S2O3 (2 mL) when complete as indicated by TLC monitoring. The organic layer was isolated and concentrated in vacuo. The resulting crude product was purified by column chromatography using EtOAc/hexane gradients to yield (2S)-tert-butyl 2,5-dicyclopropyl-3-oxopyrrolidine-1-carboxylate (20) (128 mg, 45% over two steps) as a yellow oil.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customused without further purification
  3. dissolutionThis material was dissolved in CH2Cl2 (2 mL)
  4. customthe reaction quenched with sat. aq. NaHCO3 (2 mL)
  5. customThe organic layer was isolated
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-990422ac89654c95a68f6cf216b61795
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

Loading…