Methanol → (3R,4S)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylic acid

HRID 446014Notes

Reaction equation

HRID 446014 reaction equation
CO.[C:3]([O:7][C:8](=[O:38])[CH2:9][C@@:10]1([C:26]([O:28]CC2C=CC(OC)=CC=2)=[O:27])[C@H:14]([CH3:15])[CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11]1)([CH3:6])([CH3:5])[CH3:4]>[Pd].O>[C:3]([O:7][C:8](=[O:38])[CH2:9][C@@:10]1([C:26]([OH:28])=[O:27])[C@H:14]([CH3:15])[CH2:13][NH:12][CH2:11]1)([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 887MethanolHCID 712936671-benzyl 3-(4-methoxyphenyl)methyl (3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate

Product 1

HCID 71293641(3R,4S)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylic acidYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Methanol (70 ml) and 10% Pd/C (600 mg) were added to 1-benzyl 3-(4-methoxyphenyl)methyl (3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate obtained by the method of Example 4e (3.3 g, 6.63 mmol), followed by stirring at mom temperature for three days under a hydrogen atmosphere. Water (70 ml) was added to the reaction liquid, which was stirred and filtered. The filtrate was concentrated to give the title compound (1.15 g, yield: 71.3%).

Workup

  1. customobtained by the method of Example 4e (3.3 g, 6.63 mmol)
  2. stirringwas stirred
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ef5b595a1c984d989257dc8e032dae03
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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