Lithium Chloride → 1,1-Dimethylethyl 4-(2-hydroxyethyl)-3,3-dimethyl-1-piperidinecarboxylate

HRID 445086Notes

Reaction equation

HRID 445086 reaction equation
[BH4-].[Na+].[Li+].[Cl-].C([O:7][C:8]([CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:12]1([CH3:25])[CH3:24])=O)C>CCO.C1COCC1>[OH:7][CH2:8][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:12]1([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 57850280HCID 57850280, compound

Product 1

HCID 685196211,1-Dimethylethyl 4-(2-hydroxyethyl)-3,3-dimethyl-1-piperidinecarboxylateYield 59.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of NaBH4 (204 mg, 5.40 mmol) and LiCl (229 mg, 5.40 mmol) in EtOH (8 mL) was added a solution of tert-butyl 4-{(ethoxycarbonyl)methyl}-3,3-dimethylpiperidine-1-carboxylate (538 mg, 1.80 mmol) in THF (10 mL) at 0° C. After stirring for 10 h at rt, the resulting mixture was quenched with water and the product portion was extracted with Et2O. The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography (gradient: 40% EtOAc/hexane to 90% EtOAc/hexane) to provide the titled compound (275 mg, 59%).

Workup

  1. customthe resulting mixture was quenched with water
  2. extractionthe product portion was extracted with Et2O
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 chromatography (gradient: 40% EtOAc/hexane to 90% EtOAc/hexane)

Sources & evidence

ORD record
ord-6168a02fc852481da292300537a9e7ba
Source dataset
uspto-grants-2013_07
Patent number
US08476285B2

Reaction notes

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