Ethyl 3-aminocyclohexanecarboxylate → (3-Aminocyclohexyl)methanol

HRID 2167786

Reaction equation

HRID 2167786 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](OCC)=[O:15])[CH2:9]1>C1COCC1>[NH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1

Participants

4

Reactant 2

HCID 418531Ethyl 3-aminocyclohexanecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 55290182(3-Aminocyclohexyl)methanolYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
27.5 °C

Procedure

LAH (107 mg, 2.8 mmol) was added portionwise to a solution of ethyl 3-aminocyclohexanecarboxylate (320 mg, 1.87 mmol) in THF (5 mL) at 0° C. and continued stirring at 25-30° C. for 15 h. The reaction mixture was quenched with aqueous saturated sodium sulphate solution, filtered the solid precipitate, washed the solid with THF; the filtrate collected was concentrated under reduced pressure to afford 200 mg of the title compound.

Workup

  1. customThe reaction mixture was quenched with aqueous saturated sodium sulphate solution
  2. filtrationfiltered the solid precipitate
  3. washwashed the solid with THF
  4. customthe filtrate collected
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-d445681ed7bd4fad99140ec9b16f5098
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Linked notes

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