Water → rac-(1R,2R)-2-(methylamino)cyclohexan-1-ol

HRID 406017Notes

Reaction equation

HRID 406017 reaction equation
C(O[C:6](=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14])(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:6][NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10921888(1R,2R)-trans-N-Boc-2-AminocyclohexanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 12847193rac-(1R,2R)-2-(methylamino)cyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.51 g racemic trans-(2-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester were added to a suspension of 3.09 g lithium aluminium hydride in THF. The reaction mixture was heated at reflux over night. After that time subsequently 3.1 ml water, 3.1 ml sodium hydroxide solution (2M) and 3.1 ml water were added. The mixture was then stirred for 45 minutes and then filtered through celite. The celite was washed with EtOAc. The solvent was evaporated.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux over night
  3. filtrationfiltered through celite
  4. washThe celite was washed with EtOAc
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9f9e80c4270e41e28f4c7d270229b3a1
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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