Ethanol → HCID 178472434, compound

HRID 1946986Notes

Reaction equation

HRID 1946986 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.C([O-])(O)=O.[Na+].[CH3:21][CH2:22]O>>[CH2:21]([O:9][C:8]([C@H:5]1[CH2:6][CH2:7][C@H:2]([NH2:1])[CH2:3][CH2:4]1)=[O:10])[CH3:22]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium Bicarbonate2×HCID 178511567HCID 178511567, compound

Product 1

HCID 178472434HCID 178472434, compound

Procedure

A mixture of trans-4-amino-cyclohexanecarboxylic acid (15 g, 83.8 mmol), sulfuric acid (9 mL) and EtOH (400 mL) was stirred at RT overnight. A saturated aqueous solution of NaHCO3 and NaHCO3 (solid) were added until the pH of the mixture reached 7. The solvent was then removed under reduced pressure. Aqueous K2CO3 (50%) was added and the resulting mixture was extracted with EtOAc, the organic extracts dried over Na2SO4, filtered and evaporated under reduced pressure to provide trans-4-amino-cyclohexanecarboxylic acid ethyl ester (12.81 g) as a light yellow oil.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additionAqueous K2CO3 (50%) was added
  3. extractionthe resulting mixture was extracted with EtOAc
  4. dry with materialthe organic extracts dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d1daea2749884d8a8493eb96a10dc2d2
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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