Triethylamine → trans3-[(Methylsulfonyl)oxy]-4-(1,2,3-triazol-1-yl)-1-N-(tert-butoxy carbonyl) pyrrolidine

HRID 1742990ノート

反応式

HRID 1742990 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@H:7]1[C@H:11]([N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)[CH2:10][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][C@H:7]1[C@H:11]([N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)[CH2:10][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8]1)(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86748099Rac-tert-butyl (3r,4r)-3-hydroxy-4-(1h-1,2,3-triazol-1-yl)pyrrolidine-1-carboxylate

生成物 1

HCID 86748100trans3-[(Methylsulfonyl)oxy]-4-(1,2,3-triazol-1-yl)-1-N-(tert-butoxy carbonyl) pyrrolidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl sulfonyl chloride (2.84 g, 24.8 mmole) was added slowly to an ice cooled solution of trans 3-hydroxy-4-(1,2,3-triazol-1-yl)-1-N-(tert.-butoxy carbonyl) pyrrolidine (3.16 g, 12.4 mmol) and triethylamine (4.36 ml, 31.3 mmol) in dry CH2Cl2 (10 ml). The reaction mixture was stirred under N2 at room temperature for 22 hrs and washed with saturated NaHCO3 and brine solution. The dichloromethane layer was dried over Na2SO4 and concentrated to give the title product. Yield 4.0 g (97%). 1H NMR (CDCl3) δ: 1.5 (S, 9H), 3.07 (s, 3H), 4.07 (m, 4H), 5.43 (m, 2H), 7.70 (S, 1H), 7.90 (S, 1H).

後処理

  1. washwashed with saturated NaHCO3 and brine solution
  2. dry with materialThe dichloromethane layer was dried over Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-68004e40eaa2442c98c1a9e96962043b
出典データセット
uspto-grants-1994_08
特許番号
US05342846

反応ノート

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