Methanol → HCID 178501206, compound

HRID 518593Notes

Reaction equation

HRID 518593 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.S(=O)(=O)(O)O.[NH4+].[OH-].[CH3:18]O>>[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:18])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 178511566HCID 178511566, compound

Product 1

HCID 178501206HCID 178501206, compoundYield 82%

Conditions

Temperature
80 °C

Procedure

A resealable pressure bottle was charged with cis-4-aminocyclohexanecarboxylic acid (10 g, 69.8 mmol), MeOH (100 mL), and sulfuric acid (7.45 mL, 140 mmol). The vessel was sealed and the mixture stirred at 80° C. for 24 hours. The mixture was cooled to 0° C. via an ice bath and made basic with NH4OH to a pH of approximately 10. The aqueous layer was extracted with DCM (4×50 mL) and the organic layers combined, dried over sodium sulfate and concentrated to afford cis-methyl 4-aminocyclohexanecarboxylate (9 g, 82% yield) as a colorless oil. MS m/z=158.2 [M+H]. Calc'd for C8H15NO2: 157.1.

Workup

  1. customThe vessel was sealed
  2. temperatureThe mixture was cooled to 0° C. via an ice bath
  3. extractionThe aqueous layer was extracted with DCM (4×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c0cd66a44f3746ac89ad8a9ecd1ac566
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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