N-Fluorobenzenesulfonimide → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-fluoro-piperidine-3-carboxylic acid ethyl ester
反応式
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH:13]2[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)[CH2:7]1)=[O:5])[CH3:2].[Li+].CC([N-]C(C)C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:41])(=O)=O)=CC=1>>[CH2:1]([O:3][C:4]([C:6]1([F:41])[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH:13]2[O:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)[CH2:7]1)=[O:5])[CH3:2]参加物
4
実験手順
To a cold (−78° C.) solution of 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidine-3-carboxylic acid ethyl ester (300 mg, 0.98 mmol) was added 2 M LDA (0.59 ml, 1.08 mmol). The mixture was stirred for 15 minutes. N-fluorobenzenesulfonimide (341 mg, 1.08 mmol) was added and the mixture was stirred for 20 min. The reaction was quenched with sat. NH4Cl solution. The solvent was evaporated and the remaining aqueous mixture was extracted two times with EtOAc. The organic layers were pooled, dried, concentrated and absorbed on silica. Flash chromatography (heptane/EtOAc) gave 160 of the title compound as a mixture of diastereomers.
後処理
- stirringthe mixture was stirred for 20 min
- customThe reaction was quenched with sat. NH4Cl solution
- customThe solvent was evaporated
- extractionthe remaining aqueous mixture was extracted two times with EtOAc
- customdried
- concentrationconcentrated
- customabsorbed on silica
出典と根拠
- ORDレコード
- ord-fe7d077880914e2286eb26a35fc8f800
- 出典データセット
- uspto-grants-2014_04
- 特許番号
- US08697723B2
反応ノート
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