Hydrochloric Acid → (2R,3R,4R)-1-Butyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine, hydrochloride

HRID 1280802Notes

Reaction equation

HRID 1280802 reaction equation
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)[CH2:12][N:11]([CH2:22][CH2:23][CH2:24][CH3:25])[C@@H:10]1[CH2:26][O:27]CC1C=CC=CC=1)C1C=CC=CC=1.[ClH:35]>[Pd].C(O)C>[ClH:35].[CH2:22]([N:11]1[CH2:12][C@@H:13]([OH:14])[C@H:9]([OH:8])[C@H:10]1[CH2:26][OH:27])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53802070(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-butylpyrrolidine2×

Product 1

HCID 131721051(2R,3R,4R)-1-Butyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine, 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-butylpyrrolidine (Compound 10) (0.243 g,0.53 mmol), ethanol (30 ml), 10% Pd/C (0.07 g) and excess of 1 M hydro-chloric acid to convert the amine to the hydrochloride salt. (2R,3R,4R)-1-Butyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine, hydrochloride was obtained as a yellow syrup (0.098 g, yield: 82%).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-d9bcf56026b9491687030cb9b9c6d2cc
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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