Methanol → HCID 67070431, compound

HRID 1896265Notes

Reaction equation

HRID 1896265 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([C:12]([OH:14])=[O:13])[CH2:7]1.[CH3:15]O>>[NH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7005077(1S,3S)-3-Aminocyclohexanecarboxylic acid

Product 1

HCID 67070431HCID 67070431, compoundYield 90.9%

Conditions

Temperature
65 °C

Procedure

Thionyl chloride (0.6 ml) was added to a solution of trans-3-amino-cyclohexane carboxylic acid (0.5 g, 2.8 mmol) in MeOH (20 ml) at 0° C. The reaction mixture was heated to 65° C. and concentrated in vacuum. The resulting residue was partitioned between saturated sodium bicarbonate (10 ml) and extracted with ethyl acetate. The combined organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 400 mg (90.9%) of trans-methyl 3-aminocyclohexanecarboxylate as colorless liquid.

Workup

  1. concentrationconcentrated in vacuum
  2. customThe resulting residue was partitioned between saturated sodium bicarbonate (10 ml)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ecfa4c057f5a4e3cbb41df5c5a22fa50
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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