N-acetyl-4-azido-2-hydroxymethylpyrrolidine → 1-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)ethanone

HRID 1723903Notes

Reaction equation

HRID 1723903 reaction equation
[C:1]([N:4]1[CH2:8][CH:7]([N:9]=[N+]=[N-])[CH2:6][CH:5]1[CH2:12][OH:13])(=[O:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([N:4]1[CH2:8][C@@H:7]([NH2:9])[CH2:6][C@H:5]1[CH2:12][OH:13])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 23078017N-acetyl-4-azido-2-hydroxymethylpyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 450861111-((2S,4S)-4-Amino-2-(hydroxymethyl)pyrrolidin-1-yl)ethanoneYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

92.4 g of 10% Pd—C was added to a solution of 534 g of N-acetyl-4-azido-2-hydroxymethylpyrrolidine and 2.6 L of methanol, and this was hydrogenated (30 hours) at a normal pressure until the raw material disappeared, while the atmosphere in the container was substituted for hydrogen gas every one hour. After filtration, the solution was concentrated under reduced pressure to obtain 411 g of (2S, 4S)-N-acetyl-4-amino-2-hydroxymethylpyrrolidine, more specifically, (2S,4S)-(−)-1-acetyl-4-amino-2-hydroxymethyl-pyrrolidine as an oil.

Workup

  1. customthis was hydrogenated (30 hours)
  2. filtrationAfter filtration
  3. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-143e67eac0974e3298c6e852043e833f
Source dataset
uspto-grants-2009_02
Patent number
US07485665B2

Reaction notes

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