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].[C:19](C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.IC>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][O:11][CH3:19])[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4]参加物
6
反応物 3
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 0 °C
実験手順
4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (861 mg, 3.32 mmol) was dissolved in DCM (6.6 mL) then 2,6-di-tert-butyl-4-methylpyridine (1.023 g, 4.98 mmol) and AgOTf (938 mg, 3.65 mmol) were added. The reaction mixture was cooled to 0° C. and iodomethane (0.25 mL, 3.98 mmol) was added. After 4 min, the reaction mixture was diluted with DCM and it was filtered over elite. The filtrate was concentrated to a residue which was dissolved in diethyl ether. The organic solution was washed with 10% HCl and brine, then dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 80% EtOAc/Hex) to afford the title compound (479 mg, 53%).
後処理
- filtrationwas filtered over elite
- concentrationThe filtrate was concentrated to a residue which
- dissolutionwas dissolved in diethyl ether
- washThe organic solution was washed with 10% HCl and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by silica column chromatography (20% to 80% EtOAc/Hex)
出典と根拠
- ORDレコード
- ord-9ff2852cf0d5454cbd5ea9ccb6ec7c20
- 出典データセット
- uspto-grants-2014_09
- 特許番号
- US08841278B2
関連ノート
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