Phthalimide → [R]-2-[1-(Phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione

HRID 232049

반응식

HRID 232049 반응식
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@H:10](O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@@H:10]([N:18]3[C:14](=[O:24])[C:15]4[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:17]3=[O:19])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

생성물 1

HCID 14555490[R]-2-[1-(Phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 8.9 g (50 mmol) of (S)-1-phenylmethyl-3-hydroxypyrrolidine [Synth. Commun., 15, 587 (1985)], 9.8 g (50 mmol) of phthalimide, 13.1 g (50 mmol) of triphenylphosphine and 100 ml of tetrahydrofuran was added, dropwise, a solution of 8.8 g (50 mmol) of diethyl azodicarboxylate at room temperature. The reaction was stirred for 18 hours and the solvent was removed in vacuo. The residue was triturated with ether and the solid was removed by filtration and chromatographed on silica gel (E. Merck-240-400 mesh) eluting with chloroform/ethyl acetate (80:20). Fractions were combined based on thin layer chromatography and evaporated in vacuo to give 12.1 g of the title compound.

후처리

  1. additionwas added
  2. customat room temperature
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with ether
  5. customthe solid was removed by filtration
  6. customchromatographed on silica gel (E. Merck-240-400 mesh)
  7. washeluting with chloroform/ethyl acetate (80:20)
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-5247e0e7fe19404ea815cf491954b638
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851418

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