HCID 86651574, compound → HCID 86651575, compound

HRID 1696009Notes

Reaction equation

HRID 1696009 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]([CH3:14])[C@@H:9]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C>[CH3:14][C@@H:10]1[O:11][CH2:12][CH2:13][NH:8][C@H:9]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 1

HCID 86651574HCID 86651574, compound

Product 1

HCID 86651575HCID 86651575, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(2S,3R)-Ethyl 4-benzyl-2-methylmorpholine-3-carboxylate (648 mg, 2.461 mmol), ethanol (5 ml), and Pd(OH)2 (34.6 mg, 0.246 mmol) were combined in a round-bottomed flask. The mixture was vigorously stirred and purged of air using house vacuum and recharged with H2 (three times). The reaction was stirred at 20° C. for 16 h. Transferred to a Parr® shaker and pressurized to 50 psi (345 kPa) of H2 for and shaken for 2 hours. The suspension was filtered over a pad of Celite® and washed with ethanol (5 ml). The filtrate was concentrated in vacuo to afford (2S,3R)-ethyl 2-methylmorpholine-3-carboxylate (386 mg, 2.229 mmol, 91% yield) as yellow crystal upon standing.

Workup

  1. custompurged of air
  2. stirringThe reaction was stirred at 20° C. for 16 h
  3. stirringshaken for 2 hours
  4. filtrationThe suspension was filtered over a pad of Celite®
  5. washwashed with ethanol (5 ml)
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-00559e7ddd224b7c8a33136ce6650d10
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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