Hydrochloric Acid → HCID 131718417、化合物

HRID 1034492ノート

反応式

HRID 1034492 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][C@H:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.Cl>ClCCl>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O:19][CH2:18][C@@H:9]2[CH2:10][C@@H:11]([O:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:35])=[O:34])=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chloride2 回HCID 8471Triethylamine2 回HCID 10589967(2S,4R)-Tert-butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate

生成物 1

HCID 131718417HCID 131718417、化合物収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (12.0 g) in dichloromethane (180 ml) stirring under ice cooling, triethylamine (6.23 ml), p-toluenesulfonyl chloride (8.52 g) and N,N-dimethylaminopyridine (993 mg) are successively added. The mixture is heated to reflux for 3 hours, supplemented with triethylamine (0.57 ml) and p-toluenesulfonyl chloride (775 mg), and heated to reflux for 1 hour. The reaction mixture is acidified with dilute hydrochloric acid. The organic layer is taken, washed with water, dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography and recrystallized from n-hexane to give (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol p-toluenesulfonate (16.8 g). Yield: 92%. mp. 65° to 66° C. NMR δ(CDCl3) ppm: 1.42(s, 9H), 2.15 to 2.55(m, 2H), 2.45(s, 3H), 3.03(s, 3H), 3.3 to 4.5(m, 5H), 5.1 to 5.25(m, 1H), 7.35(d, J=8.0 Hz, 2H), 7.76(d, J=8.0 Hz, 2H). IR ν (CHCl3) cm-1 : 1693.

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hours
  3. temperatureheated
  4. temperatureto reflux for 1 hour
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. customrecrystallized from n-hexane

出典と根拠

ORDレコード
ord-31811f410054434c97ade05bb2bb9f36
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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