Lithium Chloride → Tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1295524Notes

Reaction equation

HRID 1295524 reaction equation
[BH4-].[Na+].[Li+].[Cl-].C[O:6][C:7]([CH:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O>CCO.C1COCC1>[C:19]([O:18][C:16]([N:10]1[CH:9]([CH2:7][OH:6])[CH2:13][O:12][C:11]1([CH3:15])[CH3:14])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 51384973-tert-Butyl 4-methyl 2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

Product 1

HCID 14409442Tert-butyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of NaBH4 (2.247 g, 59.08 mmol) and LiCl (2.505 g, 59.08 mmol) in EtOH (42 mL), siring under nitrogen at 0° C., was added (35) (7.659 g, 29.54 mmol) in THF (30 mL) dropwise. This mixture was allowed to warm to room temperature and continued stirring for 48 hours. The precipitate was filtered and washed with ethanol. The washings were concentrated and extracted with EtOAc. The organic layer was then washed with brine and dried over anhydrous Na2SO4. Column chromatography on SiO2 (1:1 EtOAc/Hexanes) was utilized to purify 6.101 g (89%) of the title compound as a white solid.

Workup

  1. customsiring under nitrogen at 0° C.
  2. filtrationThe precipitate was filtered
  3. washwashed with ethanol
  4. concentrationThe washings were concentrated
  5. extractionextracted with EtOAc
  6. washThe organic layer was then washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customto purify 6.101 g (89%) of the title compound as a white solid

Sources & evidence

ORD record
ord-dac1df96f2f741ad8fd6a325e578d3e8
Source dataset
uspto-grants-2007_07
Patent number
US07241790B2

Reaction notes

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