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

HRID 1459645Notes

Reaction equation

HRID 1459645 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, 2.1mmol), ethanol (100 ml), 10% Pd/C (0.2 g) and excess of 1M 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-0aaea86f7ef749e393e28e45ea287028
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

Loading…