Hydrochloric Acid → (2R,3R,4R)-3,4-Dihydroxy-2-hydroxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine hydrochloride

HRID 1280808Notes

Reaction equation

HRID 1280808 reaction equation
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)[CH2:12][N:11]([CH2:22][CH:23]([OH:26])[CH2:24][OH:25])[C@@H:10]1[CH2:27][O:28]CC1C=CC=CC=1)C1C=CC=CC=1.[ClH:36]>[Pd].C(O)C>[ClH:36].[OH:8][C@H:9]1[C@H:13]([OH:14])[CH2:12][N:11]([CH2:22][CH:23]([OH:26])[CH2:24][OH:25])[C@@H:10]1[CH2:27][OH:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54393635(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine2×

Product 1

HCID 69965749(2R,3R,4R)-3,4-Dihydroxy-2-hydroxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The title compound was synthesized as described for compound 9 using (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine (Compound 17) (0.424 g, 0.89 mmol), ethanol (80 ml), 10% Pd/C (0.1 g), and excess of 4 M hydrochloric acid to convert the amine to the hydrochloride salt. (2R,3R,4R)-3,4-Dihydroxy-2-hydroxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine hydrochloride was obtained as white crystals (0.216 g, yield: 100%) with melting point above 230° C. (decomposition).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-51f2136ac9614909b6cb73db077c4d89
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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