Pyridine → 1-Benzyl 3-tert-butyl 1,3-pyrazolidinedicarboxylate

HRID 1330

反応式

HRID 1330 の反応式
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[NH:2]1.N1C=CC=CC=1.[CH2:19]([O:26][C:27](Cl)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C.C(OCC)(=O)C>[C:20]1([CH2:19][O:26][C:27]([N:1]2[CH2:5][CH2:4][CH:3]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[NH:2]2)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 57015512tert-Butyl pyrazolidine-3-carboxylate

生成物 1

HCID 133415401-Benzyl 3-tert-butyl 1,3-pyrazolidinedicarboxylate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A solution of 3-pyrazolidinecarboxylic acid, 1,1-dimethylethyl ester (10.935 g., 63.5 mmol.) in dry acetonitrile (90 ml.) was cooled to 0° C. (ice-salt bath) and treated with dry pyridine (11.0 ml.) followed by a solution of benzylchloroformate (12.54 g., 10.5 ml., 69.9 mmol.) in dry acetonitrile (25 ml.). The reaction was stirred at 0° C. for 3 hours, evaporated to dryness and the syrup obtained was redissolved in ethyl acetate (250 ml.). The solution was washed with 5% sodium bicarbonate (2×25 ml.) and brine (25 ml.), dried (anhydrous sodium sulfate), filtered, evaporated to dryness and dried in vacuo. The crude product mixture was chromatographed on a silica gel column (Merck), eluting the column with ethyl acetate:hexane mixtures (1:4; 1:2) to give 11.144 g. of title product as a syrup.

後処理

  1. customevaporated to dryness
  2. customthe syrup obtained
  3. washThe solution was washed with 5% sodium bicarbonate (2×25 ml.) and brine (25 ml.)
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customdried in vacuo
  8. customThe crude product mixture was chromatographed on a silica gel column (Merck)
  9. washeluting the column with ethyl acetate
  10. customhexane mixtures (1:4; 1:2) to give 11.144 g

出典と根拠

ORDレコード
ord-8a9fc26c3201445093ccc42bd50dbc2c
出典データセット
uspto-grants-1998_03
特許番号
US05723602

関連ノート

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