HCID 66874047, compound → HCID 55300025, compound

HRID 249880Notes

Reaction equation

HRID 249880 reaction equation
[CH2:1]([C@H:3]1[CH2:8][O:7][CH2:6][C@H:5]([CH3:9])[N:4]1C(OC(C)(C)C)=O)[CH3:2]>Cl.CO>[CH2:1]([C@H:3]1[CH2:8][O:7][CH2:6][C@H:5]([CH3:9])[NH:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 66874047HCID 66874047, compound

Product 1

HCID 55300025HCID 55300025, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

(3S,5S)-tert-Butyl 3-ethyl-5-methylmorpholine-4-carboxylate (1.8 g, 7.8 mmol) was dissolved in ca. 10 M HCl in CH3OH and allowed to stir at ambient temperature. After 2.5 h, the solution was concentrated under reduced pressure. To the residue was added 1 N NaOH (20 mL) and this was extracted with CH2Cl2 (2×20 mL). The combined organics were dried (Na2SO4) and carefully concentrated under reduced pressure to give (3S,5S)-3-ethyl-5-methylmorpholine (1.0 g, quantitative). 1H NMR consistent.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionTo the residue was added 1 N NaOH (20 mL)
  3. extractionthis was extracted with CH2Cl2 (2×20 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationcarefully concentrated under reduced pressure

Sources & evidence

ORD record
ord-899bf4762b004389a60389b3cd2eadbc
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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