Sodium Nitrite → (1R,2S)-2-Aminocyclohexanemethanol

HRID 1416878Notes

Reaction equation

HRID 1416878 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1C(O)=O.[N:12]([O-])=O.[Na+]>OS(O)(=O)=O>[NH2:12][C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:3]1[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 45084901(1S,2R)-2-(Hydroxymethyl)cyclohexane-1-carboxylic acid

Product 1

HCID 2724653(1R,2S)-2-Aminocyclohexanemethanol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

The hydrazide of (1S,2R)-2-hydroxymethyl-1-cyclohexanecarboxylic acid (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5° C, followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (1S,2R)-1-amino-2-(hydroxymethyl)cyclohexane is isolated as a light yellow

Workup

  1. extractionextraction of the reaction mixture with ethyl acetate
  2. extractionfollowed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether
  3. dry with materialdrying of the extracts over MgSO4, filtration
  4. customthe removal of solvent
  5. customby rotary evaporation

Sources & evidence

ORD record
ord-67153227aa304517a461624e30a96b17
Source dataset
uspto-grants-1999_06
Patent number
US05916786

Reaction notes

Loading…