Sodium Hydroxide → HCID 59433298, compound

HRID 60285Notes

Reaction equation

HRID 60285 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:21])([C:14](OC(C)(C)C)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[AlH4-].[Li+].[OH-].[Na+]>C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:14][OH:15])([CH3:21])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 58365057HCID 58365057, compound

Product 1

HCID 59433298HCID 59433298, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of tert-butyl 1-benzyl-4-methylpiperidine-4-carboxylate (4.7 g, 18 mmol) in diethyl ether (47 mL) was cooled at 0° C. and to this was added lithium tetrahydroaluminate (990 mg, 25 mmol) portion-wise. The reaction mixture was warmed to ambient temperature and stirred vigorously for 1 hour. The mixture was then cooled to 0° C. and a 1N solution of sodium hydroxide (6 mL) was added dropwise to the reaction mixture producing a white precipitate. The mixture was filtered and the solids were washed with ethyl acetate (100 mL). The combined filtrate was separated and the aqueous portion was extracted with ethyl acetate (2×50 mL). The combined organic portions were dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 80 g, ISCO, 45-100% ethyl acetate in heptane) to afford the title compound as a white solid, which was used in the next step without any further purification (2.7 g, 67%).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. customproducing a white precipitate
  3. filtrationThe mixture was filtered
  4. washthe solids were washed with ethyl acetate (100 mL)
  5. customThe combined filtrate was separated
  6. extractionthe aqueous portion was extracted with ethyl acetate (2×50 mL)
  7. dry with materialThe combined organic portions were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified flash chromatography (silica, 80 g, ISCO, 45-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6836beec324246a685d587e0bfc5da19
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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