Methanol → (1S,2R)-Methyl 2-aminocyclohexanecarboxylate

HRID 7020Notes

Reaction equation

HRID 7020 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[C:12]([OH:14])=[O:13].[CH3:15]O>>[CH3:15][O:13][C:12]([C@H:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C@H:6]1[NH2:5])=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7128325HCID 7128325, compound

Product 1

HCID 11008182(1S,2R)-Methyl 2-aminocyclohexanecarboxylate

Procedure

Thionyl chloride (4.73 mL, 64.8 mmol) was slowly added to a chilled (ice-water bath) suspension of (1S,2R)-2-aminocyclohexanecarboxylic acid (16.2 mmol) in anhydrous methanol (200 mL). After complete addition, the cold bath was removed and the resulting mixture warmed to room temperature. After 24 h, the reaction mixture was evaporated to dryness under a stream of dry nitrogen. The crude product, (1S,2R)-2-aminocyclohexanecarboxylic acid methyl ester, was obtained as a white solid and used in the next step without purification or characterization.

Workup

  1. temperaturea chilled
  2. additionAfter complete addition
  3. customthe cold bath was removed
  4. customthe reaction mixture was evaporated to dryness under a stream of dry nitrogen

Sources & evidence

ORD record
ord-cc8ca99006cd4d0180935677cde6acc1
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Reaction notes

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