HCID 59764941, compound → HCID 86621725, compound

HRID 406506Notes

Reaction equation

HRID 406506 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:26])[CH2:14][NH:15]C(OCC2C=CC=CC=2)=O)[C@H:9]1[CH3:27])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[NH2:15][CH2:14][C:13]([N:10]1[CH2:11][CH2:12][C@@H:8]([NH:7][C:6](=[O:28])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C@@H:9]1[CH3:27])=[O:26]

Participants

5

Reactant 2

HCID 59764941HCID 59764941, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86621725HCID 86621725, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To [(2S,3R)-1-(2-benzyloxycarbonylamino-acetyl)-2-methyl-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (example #14) (0.75 g, 1.916 mmol) in ethanol (101 mL) was added 10% palladium on carbon (0.020 g, 0.19 mmol). The flask was fitted with a hydrogen balloon and hydrogenated for about 16 h. The reaction mixture was filtered, washing with EtOH. The filtrate was concentrated under reduced pressure to afford tert-butyl (2S,3R)-1-(2-aminoacetyl)-2-methylpyrrolidin-3-ylcarbamate (0.50 g, 1.9 mmol). RP-HPLC (Table 1, Method d) Rt 3.05; m/z: (M+H)+ 258.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashing with EtOH
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ef20efb70154f898411071d2cf0e150
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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