反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][OH:11])[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].[F:19][C:20]([F:28])(S(F)(=O)=O)C(O)=O>CC#N.[Cu]I>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][O:11][CH:20]([F:28])[F:19])[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4]参加物
5
反応物 2
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 45 °C
実験手順
4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (584 mg, 2.25 mmol) and CuI (86 mg, 0.45 mmol) were suspended in MeCN (10 mL). The reaction mixture was heated to 45° C. and difluoro-fluorosulfonyl-acetic acid (0.465 mL, 4.5 mmol) was added dropwise over the course of 30 min. Stirring was continued for another 3 h, after which the reaction mixture was cooled to RT and concentrated. The residue was taken up in EtOAc and washed with saturated aqueous NaHCO3 and brine then dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (19% to 40% EtOAc/Hex) to afford the title compound (394 mg, 57%).
後処理
- temperatureafter which the reaction mixture was cooled to RT
- concentrationconcentrated
- washwashed with saturated aqueous NaHCO3 and brine
- dry with materialthen dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by silica column chromatography (19% to 40% EtOAc/Hex)
出典と根拠
- ORDレコード
- ord-d6c2ba39981e48c8a5aae565642acb2f
- 出典データセット
- uspto-grants-2012_01
- 特許番号
- US08088368B2
関連ノート
読み込み中…