Hydrochloric Acid → 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-1-propyl-, (2R,3R,4R)-

HRID 1280805Notes

Reaction equation

HRID 1280805 reaction equation
[CH2:1]([N:4]1[CH2:8][C@@H:7]([O:9]CC2C=CC=CC=2)[C@H:6]([O:17]CC2C=CC=CC=2)[C@H:5]1[CH2:25][O:26]CC1C=CC=CC=1)[CH:2]=[CH2:3].Cl>[Pd].C(O)C>[OH:17][C@H:6]1[C@H:7]([OH:9])[CH2:8][N:4]([CH2:1][CH2:2][CH3:3])[C@@H:5]1[CH2:25][OH:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54476962(2R,3R,4R)-1-allyl-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine2×

Product 1

HCID 103972923,4-Pyrrolidinediol, 2-(hydroxymethyl)-1-propyl-, (2R,3R,4R)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The title compound was synthesized as described for compound 9 using (2R,3R,4R)-1-allyl-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (compound 14) (0.910 g, 2.1 mmol), ethanol (100 ml), 10% Pd/C (0.2 g) and excess of 1 M hydrochloric acid to convert the amine to the hydrochloride salt. After evaporation of the solvent in vacuo the compound was purified on silica gel (Eluent: 2-propanol/25% ammonium hydroxide (4:1)) and (2R,3R,4R)-3,4-dihydroxy-2-hydrox-ymethyl-1-propylpyrrolidine was obtained as a yellow crystals (0.279 g, yield: 78%). Melting point: 79-80° C.

Workup

  1. customThe title compound was synthesized
  2. customAfter evaporation of the solvent in vacuo the compound
  3. customwas purified on silica gel (Eluent: 2-propanol/25% ammonium hydroxide (4:1))

Sources & evidence

ORD record
ord-9351cb53eb6948688fd7998cee63398c
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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