4-Benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester → 6,6-Dimethylmorpholine-3-carboxylic acid

HRID 12191Notes

Reaction equation

HRID 12191 reaction equation
C([O:8][C:9]([CH:11]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[CH2:13][N:12]1CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1>CC(O)=O.CO.[OH-].[OH-].[Pd+2]>[CH3:17][C:14]1([CH3:18])[CH2:13][NH:12][CH:11]([C:9]([OH:10])=[O:8])[CH2:16][O:15]1

Participants

4

Reactant 1

HCID 671657664-Benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester2×

Product 1

HCID 457913486,6-Dimethylmorpholine-3-carboxylic acidYield 95.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of 4-benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester (Intermediate 18, 1.25 g) in 40 ml of 10% AcOH/MeOH (under nitrogen) was added 250 mg of 20% Pd(OH)2 on charcoal. The reaction mixture was purged with hydrogen (balloon) and was stirred at ambient temperature for 72 hrs. To the resulting gray mixture was added 4 ml of water to help dissolution. The catalyst was removed by filtration and the filtrate was concentrated to dryness. The residue was co-evaporated with ethanol (2×) and then triturated with EtOAc. The generated white solid was filtered off and dried under high vacuum to give 559 mg of 6,6-dimethyl-morpholine-3-carboxylic acid (95% yield).

Workup

  1. customThe reaction mixture was purged with hydrogen (balloon)
  2. additionTo the resulting gray mixture was added 4 ml of water
  3. dissolutiondissolution
  4. customThe catalyst was removed by filtration
  5. concentrationthe filtrate was concentrated to dryness
  6. customtriturated with EtOAc
  7. filtrationThe generated white solid was filtered off
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-d6731d9b8e144b0e9b60dee94349263b
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Reaction notes

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