Ethyl trifluoroacetate → HCID 178523812, compound

HRID 2402597Notes

Reaction equation

HRID 2402597 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.C[O-].[Na+].[F:13][C:14]([F:21])([F:20])[C:15](OCC)=[O:16]>O1CCOCC1>[F:13][C:14]([F:21])([F:20])[C:15]([NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1)=[O:16]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 178479278HCID 178479278, compound

Product 1

HCID 178523812HCID 178523812, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

25 g of trans-4-aminocyclohexanol hydrochloride were suspended in 250 mL of dry dioxane and 30 mL of sodium methylate solution (30% in methanol, 1 equivalent) were added. 39.3 mL of ethyl trifluoroacetate were added and the reaction mixture was allowed to stir until the reaction was complete. The reaction mixture was evaporated, taken up in 50 mL of 0.1 N HCl and extracted several times with dichloromethane:isopropanol 3:1. The combined organic layer was extracted once with 0.1 N HCl and brine, dried over sodium sulfate and evaporated to dryness to yield 29.0 g of 148. Rt=0.69 min (Method C). Detected mass: 212.2 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted several times with dichloromethane:isopropanol 3:1
  3. extractionThe combined organic layer was extracted once with 0.1 N HCl and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-72645bd897e245a79b66788531a48334
Source dataset
uspto-grants-2014_08
Patent number
US08796458B2

Reaction notes

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