Diethyl Ether → benzyl (S)-2-oxo-1-((1S,2R)-4-oxo-2-propylcyclohexyl)pyrrolidin-3-ylcarbamate

HRID 1171526Notes

Reaction equation

HRID 1171526 reaction equation
[Si]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]2=[O:31])[C@H:11]([CH2:32][CH2:33][CH3:34])[CH2:10]1)(C(C)(C)C)(C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC>CC(O)=O.C1COCC1.O>[O:31]=[C:16]1[C@@H:17]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:18][CH2:19][N:15]1[C@H:12]1[CH2:13][CH2:14][C:9](=[O:8])[CH2:10][C@H:11]1[CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087Triacetoxyperiodinane2×HCID 86596863HCID 86596863, compound

Product 1

HCID 86596864benzyl (S)-2-oxo-1-((1S,2R)-4-oxo-2-propylcyclohexyl)pyrrolidin-3-ylcarbamateYield 37.3%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A sample of benzyl (S)-1-((1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-propylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (0.4 g, 0.82 mmol) was dissolved in 36 mL of 4:1:1 HOAc/THF/water and stirred at RT for 5 days. The volatiles were removed in vacuo and the residue was dissolved in EtOAc. The organic phase was washed with sat. NaHCO3, dried (MgSO4), filtered, and concentrated in vacuo. The residue was dissolved in methylene chloride (4 mL) and the resultant solution was cooled to 0° C. and charged with Dess-Martin periodinane (0.54 g, 1.27 mmol). After stirring for 2 h at RT, the solution was again cooled to 0° C. and charged with Dess-Martin periodinane (0.27 g). The reaction was stirred at RT for 14 h and treated with Et2O. The resultant suspension was washed with 1 N NaOH, sat. Na2S2O3, and sat. NaHCO3. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to afford benzyl (S)-2-oxo-1-((1S,2R)-4-oxo-2-propylcyclohexyl)pyrrolidin-3-ylcarbamate (114 mg). MS found: (M+Na)+=395.4.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic phase was washed with sat. NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in methylene chloride (4 mL)
  8. temperaturethe resultant solution was cooled to 0° C.
  9. stirringAfter stirring for 2 h at RT
  10. temperaturethe solution was again cooled to 0° C.
  11. stirringThe reaction was stirred at RT for 14 h
  12. washThe resultant suspension was washed with 1 N NaOH, sat. Na2S2O3, and sat. NaHCO3
  13. dry with materialThe organic phase was dried (MgSO4)
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f2f0847210246a08ef143e95461a7d6
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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