Sodium Hydroxide → [4-[Cyclopropyl(oxetan-3-yl)amino]cyclohexyl]methanol

HRID 1036021Notes

Reaction equation

HRID 1036021 reaction equation
[CH:1]1([N:4]([CH:16]2[CH2:19][O:18][CH2:17]2)[CH:5]2[CH2:10][CH2:9][CH:8]([C:11](OCC)=[O:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH:1]1([N:4]([CH:16]2[CH2:19][O:18][CH2:17]2)[CH:5]2[CH2:6][CH2:7][CH:8]([CH2:11][OH:12])[CH2:9][CH2:10]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67126835Ethyl 4-[cyclopropyl(oxetan-3-yl)amino]cyclohexane-1-carboxylate

Product 1

HCID 67126731[4-[Cyclopropyl(oxetan-3-yl)amino]cyclohexyl]methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 329B (1.2 g) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (0.681 g). The mixture was stirred overnight. 2N aqueous NaOH solution was added dropwise to the reaction mixture. The mixture was then diluted with ethyl acetate (300 mL) and washed with water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-450c08a2ffce49dd87d398a6e9c138b8
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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