Methanol → HCID 178501210, compound

HRID 1631318Notes

Reaction equation

HRID 1631318 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.O=S(Cl)[Cl:13].[CH3:15]O>>[ClH:13].[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:15])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178511567HCID 178511567, compound

Product 1

HCID 178501210HCID 178501210, compoundYield 96.1%

Conditions

Temperature
-10 °C

Procedure

(Trans)-4-aminocyclohexanecarboxylic acid (200 mg, 1.40 mmol) was suspended in MeOH (5.5 mL) and cooled to −10° C. To this was added SOCl2 (204 μL, 2.79 mmol) dropwise and the mixture stirred for 15 minutes. The reaction mixture was warmed to ambient temperature for 15 minutes, followed by heating at reflux for 1 hour. After cooling, the mixture was concentrated to afford the title compound (260 mg, 96.1% yield). MS (apci) m/z=158.0 (M+H).

Workup

  1. temperatureThe reaction mixture was warmed to ambient temperature for 15 minutes
  2. temperatureby heating
  3. temperatureat reflux for 1 hour
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-b70d1fa91ad545e0a8c9154673c25eef
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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