HCID 86637424, compound → HCID 58017434, compound

HRID 452009Notes

Reaction equation

HRID 452009 reaction equation
[OH:1][CH2:2][C@@H:3]([N:11](C([O-])=O)[NH:12]C([O-])=O)[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1>CO.[OH-].[OH-].[Pd+2]>[NH:11]([C@@H:3]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1)[CH2:2][OH:1])[NH2:12]

Participants

4

Reactant 1

HCID 86637424HCID 86637424, compound

Product 1

HCID 58017434HCID 58017434, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To the solution of 1-((2S)-1-hydroxy-3-(tetrahydro-2H-pyran-3-yl)propan-2-yl)hydrazine-1,2-dicarboxylate (14.68 g, 0.0332 mol) in methanol (250 mL) was added Pd(OH)2/C (1.47 g). The reaction flask was degassed and filled into H2. Stirring was continued until the starting material disappeared. When the reaction was over, the mixture was filtered through celite, and the filter cake was washed with MeOH (2×20 mL). The combined organic solvent was dried over Na2SO4, and concentrated in vacuo to give (2S)-2-hydrazinyl-3-(tetrahydro-2H-pyran-3-yl)propan-1-ol (5.79 g, 94%), which was used for the next step without purification.

Workup

  1. customThe reaction flask was degassed
  2. additionfilled into H2
  3. filtrationwas filtered through celite
  4. washthe filter cake was washed with MeOH (2×20 mL)
  5. dry with materialThe combined organic solvent was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53b5e732519c4160b7282a2f47db55e0
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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