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4-Fluorophenol → (7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(5-cyanophenyl)-1,2,3,4,6,7,8,8 a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 861349
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HRID 861349 반응식
[OH:1][CH2:2][C@@H:3]1[CH2:19][N:6]2[CH2:7][CH2:8][N:9]([C:11]3[CH:16]=[CH:15][C:14](C#N)=[CH:13][CH:12]=3)[CH2:10][C@@H:5]2[CH2:4]1.[F:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:47]([C:54](OCC)=O)=NC(OCC)=O>C1COCC1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:1][CH2:2][C@@H:3]2[CH2:19][N:6]3[CH2:7][CH2:8][N:9]([C:11]4[CH:12]=[C:13]([C:54]#[N:47])[CH:14]=[CH:15][CH:16]=4)[CH2:10][C@@H:5]3[CH2:4]2)=[CH:23][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57229001(7S,8aS)-7-hydroxymethyl-2-(4-cyanophenyl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

생성물 1

HCID 67648213(7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(5-cyanophenyl)-1,2,3,4,6,7,8,8 a-octahydro-pyrrolo[1,2-a]pyrazine수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 0.25 g (0.97 mmol) of (7S,8aS)-7-hydroxymethyl-2-(4-cyanophenyl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 16), 0.164 g (1.46 mmol) of 4-fluorophenol, 0.31 g (1.15 mmol) of triphenylphosphine in 10 mL of THF was treated with 0.18 mL (1.15 mmol) of diethyl azodicarboxylate and the solution stirred at ambient temperature for 16 h. The solvent was removed by rotary evaporation, and the residue partitioned between chloroform and 1M sodium hydroxide. The layers were separated, and the organic phase was dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 1:1 ethyl acetate:hexane gave 0.225 g (66%) of the title compound. mp (.HCl) 81°-85° C. HRMS calcd for C21H23FN3O (MH+): 352.1825, found: 352.1817.

후처리

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue partitioned between chloroform and 1M sodium hydroxide
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash silica gel chromatography with 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-fa9c9f61f32044c98a357e147565c601
출처 데이터셋
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05714487

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