Hydrochloric Acid → HCID 53898895, compound

HRID 618186Notes

Reaction equation

HRID 618186 reaction equation
C([N:8]1[CH2:12][C@@H:11]([O:13]CC2C=CC=CC=2)[C@H:10]([O:21]CC2C=CC=CC=2)[CH:9]1[CH:29]([OH:31])[CH3:30])C1C=CC=CC=1.Cl>[Pd].C(O)C>[OH:31][CH:29]([CH:9]1[C@@H:10]([OH:21])[C@H:11]([OH:13])[CH2:12][NH:8]1)[CH3:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54215364HCID 54215364, compound

Product 1

HCID 53898895HCID 53898895, compoundYield 111.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (3R,4R)-1-benzyl-3,4-dibenzyloxy-2-(1-hydroxyethyl)pyrrolidine (90 mg, 0.22 mmol) in abs. ethanol (10 ml) was added palladium on activated charcoal (10% Pd, 30 mg) and 37% hydrochloric acid (0.1 ml). The mixture was hydrogenated in a Parr apparatus at 40 psi for 20 hours. The mixture was filtered and evaporated to dryness in vacuo to give (3R,4R)-2-(1-hydroxyethyl)-3,4-pyrrolidinediol (36 mg, yield: 90%) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a7a78e82c11f4b938020c8ecf2131c6d
Source dataset
uspto-grants-1999_09
Patent number
US05952363

Reaction notes

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