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

HRID 1162508Notes

Reaction equation

HRID 1162508 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 9B (3.86 g, 11.3 mmol) in methanol:water (2:1, 50 mL) was added hydroxylamine hydrochloride salt (3.0 g) followed by pyridine (5.0 mL). The reaction was stirred at rt for 18 hr. Extract product into EtOAc, washing once with sat. 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. 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-25376ce7a6cd4173871c8319a21f5738
Source dataset
uspto-grants-2010_10
Patent number
US07820702B2

Reaction notes

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