Methanol → Methyl (1S,3R)-3-aminocyclohexane-1-carboxylate

HRID 1896294

Reaktionsgleichung

Reaktionsgleichung von HRID 1896294
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

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7005079rac-(1R,3S)-3-aminocyclohexane-1-carboxylic acid

Produkt 1

HCID 68466059Methyl (1S,3R)-3-aminocyclohexane-1-carboxylateAusbeute 90,9 %

Versuchsvorschrift

Thionyl chloride (0.6 ml) was added to solution of cis-3-amino-cyclohexanecarboxlic acid (bought from AMRI, USA, cat.-no.: A00342, 0.50 g, 2.80 mmol) in MeOH (20 ml) at 0° C. and stirred at reflux for 12 h. The volatiles were evaporated in vacuo and the resulting residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The separated organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuo to afford 400 mg (90.9%) of cis-methyl 3-aminocyclohexanecarboxylate as colorless liquid.

Aufarbeitung

  1. temperatureat reflux for 12 h
  2. customThe volatiles were evaporated in vacuo
  3. customthe resulting residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4455efa5a6e94d9598cefefae388870f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518948B2

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