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

HRID 2168101Notes

Reaction equation

HRID 2168101 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-52a9551c4bb94657b31403f88348f690
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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