Iodine → (3S,4S)-(+)-1-Benzyl-3,4-pyrrolidindiol

HRID 1081436노트

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HRID 1081436 반응식
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

참가 물질

7

반응물 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 729946(3R,4R)-1-benzyl-3,4-dihydroxypyrrolidine-2,5-dioneHCID 178418435HCID 178418435, 화합물

생성물 1

HCID 2734057(3S,4S)-(+)-1-Benzyl-3,4-pyrrolidindiol수율 53.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-41870a1c10534d18a333e4661a39e5df
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05585500

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