Pyridine → (2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyiminoethyl)pyrrolidine

HRID 501616Notes

Reaction equation

HRID 501616 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@@H:9]1[CH:21](O)[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:25][OH:26].N1C=CC=CC=1>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[C:21](=[N:25][OH:26])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 66863428(2S,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyethyl)pyrrolidine

Product 1

HCID 86594305(2R,3S)-N-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-(1-hydroxyiminoethyl)pyrrolidineYield 71.6%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 61D (3.86 g, 11.3 mmol) in methanol:water (2:1, 50 mL) was added hydroxylamine HCl salt (3.0 g) followed by pyridine (5.0 mL). The reaction was stirred at rt for 18 h. Extract product into EtOAc, washing once with sat'd aqueous NaHCO3 and once with water. Back extract the aqueous washings with EtOAc and combine this with the initial extract. Dry organic extract over MgSO4, filter and concentrate. Dilute residue in toluene and remove solvent under vacuum to provide the title compound as a white solid (2.9 g). MS (ES) m/z 359.30 [M+H]+

Workup

  1. washExtract product into EtOAc, washing once with sat'd aqueous NaHCO3 and once with water
  2. extractionBack extract
  3. washthe aqueous washings with EtOAc
  4. extractioninitial extract
  5. extractionDry organic extract over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customDilute residue in toluene and remove solvent under vacuum

Sources & evidence

ORD record
ord-afd3620f8e4b47959996a712a46c3d91
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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