Triethylammonium formate → HCID 59201303, compound

HRID 451826Notes

Reaction equation

HRID 451826 reaction equation
[Si](O[CH2:9][C@H:10]([CH2:26][CH2:27][O:28]S(C)(=O)=O)[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(C(C)(C)C)(C)C.CCN(CC)CC.C(O)=O>C1COCC1.CC(=O)OCC>[CH3:18][C:14]1([CH3:17])[N:13]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@@H:12]([CH2:11][C@H:10]2[CH2:26][CH2:27][O:28][CH2:9]2)[CH2:16][O:15]1

Participants

5

Reactant 2

HCID 11084032Triethylammonium formateHCID 86639451HCID 86639451, compound

Product 1

HCID 59201303HCID 59201303, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methylsulfonyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate (6.2 g) in 200 mL of THF was added TEAF. The reaction mixture was stirred for 12 h under reflux. The mixture was diluted with EA, washed with water back extracted EA. The combined organic layer was washed with brine, filtered, and concentrated. The crude product was purified by flash column to give the pure product (S)-tert-butyl 2,2-dimethyl-4-(((S)-tetrahydrofuran-3-yl)methyl)oxazolidine-3-carboxylate (2.4 g, 67%).

Workup

  1. temperatureunder reflux
  2. washwashed with water back extracted EA
  3. washThe combined organic layer was washed with brine
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column

Sources & evidence

ORD record
ord-59ffbf98deaf4dc8aaea2b4284e0ad96
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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