Tetrahydrofuran → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-t-butyldimethylsilyloxypropyl)-2-oxopyrrolidine

HRID 323494

반응식

HRID 323494 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:8]1=[O:23].O1CCCC1.C([Li])(CC)C.[F:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46]Br)=[CH:44][CH:43]=1>C(OCC)(=O)C.CCCCCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:46][C:45]2[CH:48]=[CH:49][C:42]([F:41])=[CH:43][CH:44]=2)([CH2:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:8]1=[O:23]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 680214-Fluorobenzyl bromideHCID 220094511-(3,4,5-Trimethoxybenzyl)-3-(3-(t-butyldimethylsilyloxy)propyl)-2-oxopyrrolidineHCID 178418400CID 53628100

생성물 1

HCID 184646181-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-t-butyldimethylsilyloxypropyl)-2-oxopyrrolidine

시약·촉매·용매 2

HCID 962Water용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
-78 °C

실험 절차

Combine 1-(3,4,5-trimethoxybenzyl)-3-(3-(t-butyldimethylsilyloxy)propyl)-2-oxopyrrolidine (0.71 g, 1.62 mmol) and tetrahydrofuran (10 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of sec-butyl lithium (1.37 mL, 1.3 M in hexane, 1.78 mmol). After 30 minutes, add 4-fluorobenzyl bromide (0.34 g, 1.78 mmol). After 15 minutes, warm slowly to ambient temperature. After 12 hours, add water and extract three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give the title compound.

후처리

  1. waitAfter 15 minutes
  2. temperaturewarm slowly to ambient temperature
  3. waitAfter 12 hours
  4. extractionextract three times with ethyl acetate
  5. dry with materialDry the combined organic layers over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue

출처 및 근거

ORD 기록
ord-b96792c495954cdcacfd5987bd81e23e
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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