Potassium Hydroxide → HCID 68647003、化合物

HRID 1162725ノート

反応式

HRID 1162725 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH:13]2[CH2:15][CH2:14]2)[CH:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:33]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)C(C)C)C.[OH-].[K+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH:13]2[CH2:15][CH2:14]2)[CH:10]([NH2:33])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 686471701,3-Pyrrolidinedicarboxylic acid, 4-cyclopropyl-, 1-(1,1-dimethylethyl) ester, (3R,4R)-rel-

生成物 1

HCID 68647003HCID 68647003、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

101.5 To a stirred solution of 200 mg (3RS,4RS)-4-cyclopropyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester at 80° C. in 2 ml dioxane under an argon atmosphere were added 0.20 ml diphenylphosphoryl azide and 0.16 ml N-ethyldiisopropylamine. Stirring at 80° C. was continued for 4 hrs. Then, the hot mixture was poured onto 15 ml 1 N KOH and the product was extracted with EtOAc. The aqueous phase was back extracted with EtOAc. The combined organics were washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 34 mg (3RS,4SR)-3-amino-4-cyclopropyl-pyrrolidine-1-carboxylic acid tert-butyl ester as light brown gum. MS 227.3 ([M+H]+)

後処理

  1. extractionthe product was extracted with EtOAc
  2. extractionThe aqueous phase was back extracted with EtOAc
  3. washThe combined organics were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

出典と根拠

ORDレコード
ord-98c372525607423e84885757efd00361
出典データセット
uspto-grants-2010_10
特許番号
US07820699B2

反応ノート

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