1-benzyl 3-(4-methoxyphenyl)methyl (3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate → (3R,4S)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylic acid

HRID 446015Notes

Reaction equation

HRID 446015 reaction equation
[C:1]([O:5][C:6](=[O:36])[CH2:7][C@@:8]1([C:24]([O:26]CC2C=CC(OC)=CC=2)=[O:25])[C@H:12]([CH3:13])[CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:36])[CH2:7][C@@:8]1([C:24]([OH:26])=[O:25])[C@H:12]([CH3:13])[CH2:11][NH:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 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 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methanol (3 ml) and 10% Pd/C (30 mg) were added to 1-benzyl 3-(4-methoxyphenyl)methyl (3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate which is obtained in Example 4d and which is without silica gel column chromatography purification (104 mg, 0.21 mmol), followed by stirring at mom temperature overnight under a hydrogen atmosphere. Water was added to the reaction liquid, which was stirred and filtered. The filtrate was concentrated to give the title compound (48.7 mg, yield: 95.3%).

Workup

  1. customis obtained in Example 4d and which
  2. customis without silica gel column chromatography purification (104 mg, 0.21 mmol)
  3. additionWater was added to the reaction liquid, which
  4. stirringwas stirred
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2830580354b84c62bd46ae510ff66013
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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