Hydrochloric Acid → HCID 86724517, compound

HRID 1852770Notes

Reaction equation

HRID 1852770 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 APCI 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-f63de4fd876f462a8d64f252bc819c9d
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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