Lithium aluminum hydride → HCID 58365113, compound

HRID 60296Notes

Reaction equation

HRID 60296 reaction equation
[CH2:1]([C:3]1([C:16](OC(C)(C)C)=[O:17])[CH2:8][CH2:7][N:6]([C:9](OC(C)(C)C)=O)[CH2:5][CH2:4]1)[CH3:2].[AlH4-].[Li+]>O1CCCC1.[OH-].[Na+]>[CH2:1]([C:3]1([CH2:16][OH:17])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 67298746Di-tert-butyl 4-ethylpiperidine-1,4-dicarboxylate

Product 1

HCID 58365113HCID 58365113, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred suspension of di-tert-butyl 4-ethylpiperidine-1,4-dicarboxylate (1.1 g, 3.7 mmol) in tetrahydrofuran (13 mL) was added lithium tetrahydroaluminate (1.0N solution in tetrahydrofuran, 15 mL, 15 mmol), and the mixture was stirred at ambient temperature for 6 hours. The mixture was diluted with a 1N sodium hydroxide solution (5 mL), filtered over Whatman filter paper, and the solids were washed with ethyl acetate (50 mL). The combined filtrate was separated, and the organic portion was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a white solid, which was used in the next step without any further purification (506 mg, 57%).

Workup

  1. filtrationfiltered over Whatman
  2. filtrationfilter paper
  3. washthe solids were washed with ethyl acetate (50 mL)
  4. customThe combined filtrate was separated
  5. dry with materialthe organic portion was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-942c7aa5ec8b443fa9511366a4107558
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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