2-(Hydroxymethyl)pyrrolidine-3,4-diol → 1,4-Dideoxy-1,4-imino-d-arabinitol

HRID 429331Notes

Reaction equation

HRID 429331 reaction equation
[OH:1][CH:2]1[CH:6]([OH:7])[CH2:5][NH:4][CH:3]1[CH2:8][OH:9].[C:10]([C@H:13]([C@@H:15]([C:17]([O-:19])=[O:18])[OH:16])[OH:14])([O-:12])=[O:11].C(O[C@H]1[C@H](OCC2C=CC=CC=2)[C@@H](COCC2C=CC=CC=2)NC1)C1C=CC=CC=1>C(O)(=O)C.CO.[Pd]>[OH:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][NH:4][C@@H:3]1[CH2:8][OH:9].[C:10]([C@H:13]([C@@H:15]([C:17]([O-:19])=[O:18])[OH:16])[OH:14])([O-:12])=[O:11]

Participants

8

Reactant 3

HCID 13352-(Hydroxymethyl)pyrrolidine-3,4-diolHCID 5460284D-TartrateHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine

Product 2

HCID 4519911,4-Dideoxy-1,4-imino-d-arabinitolHCID 5460284D-Tartrate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A more direct way to synthesise 3,4-dihydroxy-2-hydroxymethylpyrrolidine, D-tartrate is by reduring 2,3,5-Tri-O-benzyl-1,4-dideoxy-1,4-imino-D-arabinitol with Pd/C in glacial acetic acid. The formed, oily (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethyl-pyrrolidine,acetate is dissolved in methanol and added to a solution containing D-tartraric acid at reflux and (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine, D-tartrate is formed and can be isolated by filtration. Ion exchange chromatography is thereby avoided.

Workup

  1. additionadded to a solution
  2. additioncontaining D-tartraric acid
  3. temperatureat reflux

Sources & evidence

ORD record
ord-044689dc2fd64923adc958759ad750ed
Source dataset
uspto-grants-2001_11
Patent number
US06316489B1

Reaction notes

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