Ethyl trifluoroacetate → HCID 178523812, compound

HRID 1913138Notes

Reaction equation

HRID 1913138 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-54d2e0bc252e496d9d9465a299871496
Source dataset
uspto-grants-2013_12
Patent number
US08609691B2

Reaction notes

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