N-Fluorobenzenesulfonimide → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-fluoro-piperidine-3-carboxylic acid ethyl ester

HRID 453822노트

반응식

HRID 453822 반응식
[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]

참가 물질

4

반응물 3

HCID 588007N-FluorobenzenesulfonimideHCID 2724682Lithium diisopropylamideHCID 251754981-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidine-3-carboxylic acid ethyl ester

생성물 1

HCID 251762851-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-fluoro-piperidine-3-carboxylic acid ethyl ester

실험 절차

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.

후처리

  1. stirringthe mixture was stirred for 20 min
  2. customThe reaction was quenched with sat. NH4Cl solution
  3. customThe solvent was evaporated
  4. extractionthe remaining aqueous mixture was extracted two times with EtOAc
  5. customdried
  6. concentrationconcentrated
  7. customabsorbed on silica

출처 및 근거

ORD 기록
ord-8fb00af983d14465a30fc18cabf18fe7
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492549B2

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