Hydrochloric Acid → HCID 86724517, compound

HRID 81162Notes

Reaction equation

HRID 81162 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH3:14])[C@H:9]1[CH2:15][CH3:16])C1C=CC=CC=1.[ClH:17]>CO.[OH-].[OH-].[Pd+2]>[ClH:17].[CH2:15]([C@@H:9]1[C@@H:10]([CH3:14])[O:11][CH2:12][CH2:13][NH:8]1)[CH3:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86724516(2R,3R)-4-benzyl-3-ethyl-2-methylmorpholine

Product 1

HCID 86724517HCID 86724517, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

Pd(OH)2 (15.0 mg, 10% on carbon) was added to a solution of (2R,3R)-4-benzyl-3-ethyl-2-methylmorpholine (110 mg, 0.50 mmol) in MeOH (10 mL) under N2. Hydrogen was bubbled through the reaction mixture for one minute and then the reaction was stirred at rt under hydrogen (1 atm) for 2 hours. Then, N2 was bubbled through the reaction for 1 minute. A solution of HCl (3M, 3 mL, 9 mmol) in methanol was added. The reaction mixture was stirred at room temperature for 30 minutes and concentrated in vacuo to afford (2R,3R)-3-ethyl-2-methylmorpholine hydrochloride. 1H NMR (300 MHz, DMSO-d6) δ 9.45-9.34 (br s, 1H), 3.84-3.91 (m, 1H), 3.68-3.78 (m, 1H), 3.53-3.61 (m, 1H), 3.08-3.21 (m, 1H), 2.93-3.01 (m, 1H), 2.70-2.85 (m, 1H), 1.45-1.81 (m, 2H), 1.13 (d, J=6.3 Hz, 3H), 0.90-1.05 (m, 3H). MS APCl calc'd for C7H15NO [M+H]+ 130. found 130.

Workup

  1. customHydrogen was bubbled through the reaction mixture for one minute
  2. customThen, N2 was bubbled through the reaction for 1 minute
  3. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd0baeddecad4445a70b346acf549976
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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