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

HRID 227566Notes

Reaction equation

HRID 227566 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

Conditions

Temperature
0 °C

Procedure

To a mixture of NaBH4 (2.247 g, 59.08 mmol) and LiCl (2.505 g, 59.08 mmol) in EtOH (42 mL), stirring under nitrogen at 0° C., was added (35) (7.659 g, 29.54 mmol) in THF (30 mL) dropwise. This mixture was allowed to warn 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. customto warn to room temperature
  2. stirringcontinued stirring for 48 hours
  3. filtrationThe precipitate was filtered
  4. washwashed with ethanol
  5. concentrationThe washings were concentrated
  6. extractionextracted with EtOAc
  7. washThe organic layer was then washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customto purify 6.101 g (89%) of the title compound as a white solid

Sources & evidence

ORD record
ord-018d7a518f2c4a5cabd26bc13a623460
Source dataset
uspto-grants-2009_07
Patent number
US07560477B2

Reaction notes

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