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

HRID 232049

反応式

HRID 232049 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5247e0e7fe19404ea815cf491954b638
出典データセット
uspto-grants-1989_07
特許番号
US04851418

関連ノート

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