Iodine → 90365-74-5

HRID 1081436Notes

Reaction equation

HRID 1081436 reaction equation
II.[CH2:3]([N:10]1[C:14](=O)[C@H:13]([OH:16])[C@@H:12]([OH:17])[C:11]1=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.B.[Na].[OH-].[K+]>C1COCC1.CO>[CH2:3]([N:10]1[CH2:14][C@H:13]([OH:16])[C@@H:12]([OH:17])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 7299461-Benzyl-3,4-dihydroxypyrrolidine-2,5-dioneHCID 178418435HCID 178418435, compound

Product 1

HCID 273405790365-74-5Yield 53.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 50.7 g (0.2 mole) iodine in 200 ml THF was added dropwise to a suspension of 22.1 g (0.1 mole) (3R,4R)-1-benzyl-3,4-dihydroxy-2,5-pyrrolidinedione (IIb) and 15.2 g (0.4 mole) sodium boron hydride in 500 ml THF within 1 h at 12°-15° C. The mixture was then heated 2 d under argon on a reflux. After cooling off, 50 ml methanol were added and after the end of the development of gas the mixture was evaporated to dryness. The residue was taken up in 60 ml water and compounded with 15 ml conc. hydrochloric acid until an acidic reaction. After 30 min agitation, 150 ml 20% potash lye were added and [the mixture] extracted twice with 250 ml MTBE each time. After evaporation, 19.2 g colorless, crystalline residue remained. Recrystallization from 60 ml ethyl acetate yielded in 2 fractions 10.4 g (53.9%) (3S,4S)-1-benzyl-3,4-dihydroxypyrrolidine (IIIb).

Workup

  1. temperatureThe mixture was then heated 2 d under argon on a reflux
  2. temperatureAfter cooling off
  3. customafter the end of the development of gas the mixture was evaporated to dryness
  4. customcompounded with 15 ml conc. hydrochloric acid until an acidic reaction
  5. extraction[the mixture] extracted twice with 250 ml MTBE each time
  6. customAfter evaporation, 19.2 g colorless
  7. customRecrystallization from 60 ml ethyl acetate

Sources & evidence

ORD record
ord-41870a1c10534d18a333e4661a39e5df
Source dataset
uspto-grants-1996_12
Patent number
US05585500

Reaction notes

Loading…