2,6-Lutidine → (2S,3S)-4-(allyloxy)-3-(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyloxy)butyl acetate
Reaction equation
[C:1]([O:4][CH2:5][C@@H:6]([OH:20])[C@@H:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][O:9][CH2:10][CH:11]=[CH2:12])(=[O:3])[CH3:2].N1C(C)=CC=CC=1C.[Si:29](OS(C(F)(F)F)(=O)=O)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:1]([O:4][CH2:5][C@@H:6]([O:20][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C@@H:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][O:9][CH2:10][CH:11]=[CH2:12])(=[O:3])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
The crude material from Step 2 (0.090 g) was dissolved in CH2Cl2 (3 mL) and cooled to 0° C. To the cooled solution, was added 2,6-lutidine (0.10 mL, 0.90 mmol) followed by TBSOTf (0.10 mL, 0.4 mmol). The mixture was stirred at 0° C. for 2 h then diluted with H2O and sat'd NaHCO3. The aqueous phase was extracted with CH2Cl2 (3×20 mL) and the organic extracts dried (Na2SO4), filtered, and conc in vacuo. Purification on SiO2 (5-20% EtOAc/Hexanes) gave the title compound as a yellow oil.
Workup
- extractionThe aqueous phase was extracted with CH2Cl2 (3×20 mL)
- dry with materialthe organic extracts dried (Na2SO4)
- filtrationfiltered
- customPurification on SiO2 (5-20% EtOAc/Hexanes)
Sources & evidence
- ORD record
- ord-0d04cb9dc97042909e4928eb1ce4c7f5
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745484B2
Reaction notes
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