Sodium Methoxide → (S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate

HRID 451812Notes

Reaction equation

HRID 451812 reaction equation
C([O:5][C:6](=O)[CH2:7][CH2:8][C@@H:9]([CH2:25][NH:26][CH3:27])[CH2:10][C@H:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(C)(C)C.C[O-].[Na+]>CO>[CH3:16][C:13]1([CH3:17])[N:12]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[C@@H:11]([CH2:10][C@H:9]2[CH2:8][CH2:7][C:6](=[O:5])[N:26]([CH3:27])[CH2:25]2)[CH2:15][O:14]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59201399(S)-tert-butyl 4-((R)-5-tert-butoxy-2-((methylamino)methyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59201489(S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylateYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (S)-tert-butyl 4-((R)-5-tert-butoxy-2-((methylamino)methyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate (212 mg, 0.53 mmol) in absolute MeOH was added a NaOMe solution in MeOH (33%, 0.4 mL). The resulting solution was stirred for 24 h. The solvent was removed under reduced pressure, the residue was dissolved in EtOAc (50 mL), washed with 1 M HCl, sat. aq. NaHCO3, brine, and dried over Na2SO4, filtered and evaporated to give (S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate (160 mg, 92%). MS ESI +ve m/z 564 (M+Na).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (50 mL)
  3. washwashed with 1 M HCl, sat. aq. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-bd2228dd6968473fb12784ddce863b82
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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