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

HRID 1459640Notes

Reaction equation

HRID 1459640 reaction equation
[ClH:1].C([O:9][C@@H:10]1[C@H:14]([O:15]CC2C=CC=CC=2)[CH2:13][N:12]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C@:11]1([CH3:35])OCC1C=CC=CC=1)C1C=CC=CC=1.Cl.C([OH:39])C>[Pd]>[ClH:1].[CH:24]1([CH2:23][N:12]2[CH2:13][C@@H:14]([OH:15])[C@H:10]([OH:9])[C@H:11]2[CH2:35][OH:39])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 131721050(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxy-methyl-1-cyclopropylmethylpyrrolidine, hydrochloride2×

Product 1

HCID 70146917(2R,3R,4R)-1-cyclopropylmethyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine, hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxy-methyl-1-cyclopropylmethylpyrrolidine, hydrochloride (Compound 8) (0.14 g, 0.28 mmol) in 96% ethanol (15 ml) was added 10% Pd/C (50 mg) and 1M hydrochloric acid (0.1ml). The reaction mixture was hydrogenated in Parr apparatus at 40 psi for 24 hours. The mixture was filtered and concentrated in vacuo giving (2R,3R,4R)-1-cyclopropylmethyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine, hydrochloride as a yellow oil (0.063 g, yield: 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d27bd5dba4b3458f99940053c4e0e864
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

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