Hydrochloric Acid → HCID 57193390, compound

HRID 850288Notes

Reaction equation

HRID 850288 reaction equation
[CH2:1]([C@H:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7](=[O:16])[C@H:6]([O:17][Si](C(C)(C)C)(C)C)[C@H:5]1[O:25][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.Cl>C(O)C>[CH2:1]([C@H:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:7](=[O:16])[C@H:6]([OH:17])[C@H:5]1[OH:25])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 439655D-Tartaric acidHCID 10412681HCID 10412681, compound

Product 1

HCID 57193390HCID 57193390, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture composed of 150 g of (3R*,4S*,5R*)-5-allyl-1-benzyl-3,4-bis(tert-butyldimethylsilyloxy)-2-pyrrolidinone which had been prepared according to the procedure described in J. Org. Chem. 60, 103-108 (1995) by using D-tartaric acid as the starting material, 500 ml of ethanol, and 20 ml of concentrated hydrochloric acid was heated to 50° C. and stirred for 2 days. After the reaction mixture was concentrated under reduced pressure, water was added to the resulting residue. This mixture was washed with n-hexane and then extracted with chloroform. After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. Then, ether and n-hexane were added to the resulting residue so as to crystallize the desired product. These crystals were collected by filtration to obtain 24.8 g of (3R*,4S*,5R*)-5-allyl-1-benzyl-3,4-dihydroxy-2-pyrrolidinone.

Workup

  1. customhad been prepared
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the resulting residue
  4. washThis mixture was washed with n-hexane
  5. extractionextracted with chloroform
  6. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionThen, ether and n-hexane were added to the resulting residue so as
  9. customto crystallize the desired product
  10. filtrationThese crystals were collected by filtration

Sources & evidence

ORD record
ord-3037ccebcef749c09a164ce875cb175c
Source dataset
uspto-grants-2000_01
Patent number
US06017911

Reaction notes

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