(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide → 1-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one

HRID 906927노트

반응식

HRID 906927 반응식
CON(C)[C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:9][N:8]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7]1)=[O:5].[CH2:27]([Li])[CH3:28]>C1COCC1>[CH2:19]([N:8]1[CH2:9][CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH:6]([C:4](=[O:5])[CH2:27][CH3:28])[CH2:7]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

4

반응물 2

HCID 86627620(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amideHCID 178506846HCID 178506846, 화합물

생성물 1

HCID 671316011-[(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (described herein above) 377 mg (0.959 mmol) dissolved in THF (4 mL) was added 0.676 mL (1.15 mmol) of ethyllithium (1.7M in dibutylether) dropwise at −78° C. and stirred for one hour. The reaction was quenched by aq. ammonium chloride solution and extracted with ethylacetate. The separated organic layer was dired on anhydrous sodium sulfate and concentrated in vaccuo. The residue was purified by silica gel column chromatography eluted by a mixture of heptane and ethyl acetate (10:1) yielding 212 mg (61%) of the title compound as a light yellow oil. ES-MS m/e: 362.2 (M+H+).

후처리

  1. customThe reaction was quenched by aq. ammonium chloride solution
  2. extractionextracted with ethylacetate
  3. concentrationconcentrated in vaccuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted by a mixture of heptane and ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-2f03cbb8fe8f46d8aaee08b6b7a506d2
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012998B2

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