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

HRID 1742990노트

반응식

HRID 1742990 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-68004e40eaa2442c98c1a9e96962043b
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342846

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