1,1'-Carbonyldiimidazole → Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate

HRID 423392

反応式

HRID 423392 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=O)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].Cl.[CH3:29][NH:30][O:31][CH3:32]>ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH:22]([C:25](=[O:27])[N:30]([O:31][CH3:32])[CH3:29])[CH2:21]1)=[O:19])([CH3:14])([CH3:15])[CH3:16]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

生成物 1

HCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Add in one portion 1,1′-carbonyldiimidazole (8.3 g, 51 mmol) to a solution of pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (10.0 g, 46.5 mmol) in dichloromethane (155 mL) at RT. Allow the mixture to stir for 15 min. Add slowly N,O-dimethylhydroxylamine hydrochloride (5.4 g, 55.8 mmol). Stir the reaction mixture at RT overnight. Dilute the mixture with dichloromethane (200 mL), wash with water (2×300 mL), brine (200 mL), dry over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph and elute with 50-100% ethylacetate/hexane to give 10.8 g (90%) of the title compound. LC-MS/ES m/z 203.0 [M-tert-Bu+H]+.

後処理

  1. stirringStir the reaction mixture at RT overnight
  2. washwash with water (2×300 mL), brine (200 mL)
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude material by flash chromatograph
  7. washelute with 50-100% ethylacetate/hexane

出典と根拠

ORDレコード
ord-5a2427e5e4d943378acb9ddb6e26de1e
出典データセット
uspto-grants-2012_01
特許番号
US08101764B2

関連ノート

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