HCID 59436397, compound → HCID 59436402, compound

HRID 1961397Notes

Reaction equation

HRID 1961397 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@:4]([CH3:24])([C:14]([O:16]CC2C=CC=CC=2)=[O:15])[CH2:3]1>CO.[Pd]>[C:10]([O:9][C:7]([N:5]1[CH2:6][C@@H:2]([OH:1])[CH2:3][C@@:4]1([CH3:24])[C:14]([OH:16])=[O:15])=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 1

HCID 59436397HCID 59436397, compound

Product 1

HCID 59436402HCID 59436402, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To nitrogen flushed pressure bottle, were added Pd/C (200 mg) and (2S,4S)-2-benzyl 1-tert-butyl 4-hydroxy-2-methylpyrrolidine-1,2-dicarboxylate (1.4 g, 4.17 mmol) in MeOH (300 mL). The reaction mixture was hydrogenated at 50 psi overnight. The reaction mixture was passed through a pad of celite, washed with MeOH, and concentrated. The residue (0.86 g, 84%) was used for the next step without purification. 1H NMR (CD3OD, 400 MHz) δ 4.32-4.39 (m, 1H), 3.62-3.68 (m, 1H), 3.34-3.37 (m, 1H), 2.12-2.22 (m, 2H), 1.51 and 1.49 (s, 3H), 1.43 and 1.40 (s, 9H).

Workup

  1. customTo nitrogen flushed pressure bottle
  2. customwas hydrogenated at 50 psi overnight
  3. washwashed with MeOH
  4. concentrationconcentrated
  5. customThe residue (0.86 g, 84%) was used for the next step without purification

Sources & evidence

ORD record
ord-df07a103e04942afbd6bf25293d7671c
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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