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

HRID 2059775

Reaction equation

HRID 2059775 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-81dc67934e4448a5b7b563d5fa75a2b6
Source dataset
uspto-grants-2012_10
Patent number
US08278314B2

Linked notes

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