Hydrazine hydrate (1:1) → (2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

HRID 1034481ノート

反応式

HRID 1034481 の反応式
[N+:1]([C:4]1[CH:50]=[CH:49][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:37][N:38]2C(=O)C3=CC=CC=C3C2=O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.NN>ClCCl.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:14][C@H:13]2[CH2:37][NH2:38])=[O:11])=[CH:49][CH:50]=1)([O-:3])=[O:2]

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 57302820(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine

生成物 1

HCID 15056148(2S,4S)-2-aminomethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine収率 91%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine (10.46 g: 15.31 mmole) in a mixture of dichloromethane (80 ml) and methanol (160 ml), hydrazine hydrate (1.53 ml: 2 eq.) is added, and the mixture is concentrated to remove dichloromethane by warming and refluxed for 3 hours and 15 minutes. The reaction mixture is concentrated in vacuo. The residue is diluted with dichloromethane and filtered to remove solid. The filtrate is washed with water, dried over magnesium sulfate, and concentrated in vacuo to give crude (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-aminomethyl-4-tritylthiopyrrolidine (7.71 g). Yield: 91%. NMR δ(CDCl3 :CD3OD=2:1) ppm: 1.46 to 3.76(m, 10H), 5.04, 5.12(ABq, J=15 Hz, 2H), 7.10 to 7.56(m, 17H), 8.12 to 8.30(m, 2H). IR ν (CHCl3) cm-1 : 1695, 1606.

後処理

  1. additionis added
  2. concentrationthe mixture is concentrated
  3. customto remove dichloromethane
  4. temperatureby warming
  5. temperaturerefluxed for 3 hours and 15 minutes
  6. concentrationThe reaction mixture is concentrated in vacuo
  7. additionThe residue is diluted with dichloromethane
  8. filtrationfiltered
  9. customto remove solid
  10. washThe filtrate is washed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-20e9d589e6964e5aa9dc30ab53058dd0
出典データセット
uspto-grants-1994_05
特許番号
US05317016

反応ノート

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