4-Aminotetrahydro-2H-pyran-4-carboxylic acid hydrochloride → (4-Aminooxan-4-yl)methanol

HRID 271293

Reaction equation

HRID 271293 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl.[NH2:8][C:9]1([C:15](O)=[O:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>C1COCC1>[NH2:8][C:9]1([CH2:15][OH:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 27344004-Aminotetrahydro-2H-pyran-4-carboxylic acid hydrochlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 18316484(4-Aminooxan-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Amino-tetrahydropyran-4-yl)-methanol is prepared by adding LAH (99%, 1.2 g), portionwise, to a stirred mixture of 4-aminotetrahydropyran-4-carboxylic acid hydrochloride (2.0 g, 11.0 mmol) in THF (30 mL) at 0° C. Upon completion of addition, the reaction mixture is warmed to room temperature and stirred for 1 hour. The reaction mixture is cooled to 0° C. and cautiously quenched by the portionwise addition of Na2SO4.10H2O (4 g). The reaction mixture is diluted with ethyl acetate, warmed to room temperature, and filtered through Celite to give the desired product.

Workup

  1. custom(4-Amino-tetrahydropyran-4-yl)-methanol is prepared
  2. additionUpon completion of addition
  3. temperatureThe reaction mixture is cooled to 0° C.
  4. customcautiously quenched by the portionwise addition of Na2SO4.10H2O (4 g)
  5. additionThe reaction mixture is diluted with ethyl acetate
  6. temperaturewarmed to room temperature
  7. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-955178be882b404683e51d66c5fa93f9
Source dataset
uspto-grants-2008_11
Patent number
US07452895B2

Linked notes

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