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

HRID 1455391Notes

Reaction equation

HRID 1455391 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

Examples 2t and 2u, Step 5: 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-3fdd4a4de9e04fbf8711b8b70466be91
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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