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

HRID 446004Notes

Reaction equation

HRID 446004 reaction equation
C(O)C.[C:4]([O:8][C:9](=[O:39])[CH2:10][C@@:11]1([C:27]([O:29]CC2C=CC(OC)=CC=2)=[O:28])[C@H:15]([CH3:16])[CH2:14][N:13](C(OCC2C=CC=CC=2)=O)[CH2:12]1)([CH3:7])([CH3:6])[CH3:5]>[Pd].O>[C:4]([O:8][C:9](=[O:39])[CH2:10][C@@:11]1([C:27]([OH:29])=[O:28])[C@H:15]([CH3:16])[CH2:14][NH:13][CH2:12]1)([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 702EthanolHCID 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 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Ethanol (50 ml) and 10% Pd/C (500 mg) were added to 1-benzyl 3-(4-methoxyphenyl)methyl (3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate obtained in Example 2i (2.92 g, 5.87 mmol), followed by stirring at mom temperature for 38 hours and five minutes under a hydrogen atmosphere. Water (100 ml) was added to the reaction liquid, which was stirred and filtered. The filtrate was concentrated to give the title compound (1.37 g, yield: 95.9%).

Workup

  1. stirringwas stirred
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7b61fd75c234459894e75159b808504c
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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