Hydrochloric Acid → 1-Acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine

HRID 1280803Notes

Reaction equation

HRID 1280803 reaction equation
[C: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@@:5]1([CH3:33])OCC1C=CC=CC=1)(=[O:3])[CH3:2].[CH2:34]([OH:36])[CH3:35].Cl.C([O:45][C@H:46]1[C@H:50]([O:51]CC2C=CC=CC=2)[CH2:49][NH:48][C@@H:47]1[CH2:59][O:60]CC1C=CC=CC=1)C1C=CC=CC=1>[Pd].CO>[C:1]([N:4]1[CH2:8][C@@H:7]([OH:9])[C@H:6]([OH:17])[C@H:5]1[CH2:33][OH:36])(=[O:3])[CH3:2].[C:34]([N:48]1[CH2:49][CH:50]([OH:51])[CH:46]([OH:45])[CH:47]1[CH2:59][OH:60])(=[O:36])[CH3:35]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidineHCID 70146873(2R,3R,4R)-1-acetyl-3,4-dibenzyloxy-2-benzyloxy-methylpyrrolidine2×

Product 2

HCID 184261171-Acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidineYield 86%HCID 54463964(2R,3R,4R)-1-Acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was synthesized as described for compound 9 using (2R,3R,4R)-1-acetyl-3,4-dibenzyloxy-2-benzyloxy-methylpyrrolidine (Compound 12) (0.595 g, 1.3 mmol), ethanol (30 ml), methanol (10 ml), 10% Pd/C (0.10 g) and a catalytic amount of 1 M hydrochloric acid. Purification of the product on silica gel (Eluent: Ethyl acetate/methanol (1:1))afford-ed(2R,3R,4R)-1-acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine(0.2 g, yield: 86%) as an oil.

Workup

  1. customPurification of the product on silica gel (Eluent

Sources & evidence

ORD record
ord-0ce858f0a06f402bbfc32b6dcdd8959a
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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