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

HRID 1459643Notes

Reaction equation

HRID 1459643 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].C([OH:36])C.Cl>[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]

Participants

6

Reactant 3

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

Product 1

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 1M 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(0.2g,yield: 86%) as an oil.

Workup

  1. customPurification of the product on silica gel (Eluent: Ethyl acetate/methanol (1:1))

Sources & evidence

ORD record
ord-ab2f8ccba08d4b9db14b82613c49daaf
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

Loading…