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Triethylamine → (3S,4S)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1670619
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HRID 1670619 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([OH:24])[C@@H:21]([NH:25]CC2C=CC=CC=2)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:23][C@H:22]([OH:24])[C@@H:21]([NH:25][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[N+:9]([O-:11])=[O:10])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 11277777tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 67333783(3S,4S)-tert-butyl 3-(4-bromo-2-nitrophenylamino)-4-hydroxypyrrolidine-1-carboxylate수율 94.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-bromo-4-fluoro-3-nitrobenzene (0.125 mol, 26.0 g) in ethyl acetate (300 mL) add (3S,4S)-3-benzylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.113 mol, 23.0 g) and triethylamine (0.339 mol, 35.0 g), reflux for 14 h, cool to room temperature, and wash with water and brine. Dry over anhydrous sodium sulfate, evaporate the solvent, and purify by flash column chromatography to give the title compound as a yellow solid (43.0 g, 90%). APCI MS m/z 403 [M+H]+.

후처리

  1. temperaturereflux for 14 h
  2. washwash with water and brine
  3. dry with materialDry over anhydrous sodium sulfate
  4. customevaporate the solvent
  5. custompurify by flash column chromatography

출처 및 근거

ORD 기록
ord-cc52c384dabf4d5989895f7a18c15a44
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07994164B2

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