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

HRID 2176930

反応式

HRID 2176930 の反応式
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

参加物

4

反応物 3

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

生成物 1

HCID 68466059Methyl (1S,3R)-3-aminocyclohexane-1-carboxylate収率 90.9%

実験手順

Thionyl chloride (0.6 ml) was added to solution of cis-3-amino-cyclohexanecarboxylic 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.

後処理

  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

出典と根拠

ORDレコード
ord-3ee1ff0dd8ef4ab68d850b68e7d09664
出典データセット
uspto-grants-2015_06
特許番号
US09067888B2

関連ノート

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