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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
Notes
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Reaction equation

HRID 861349 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 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]pyrazine
Yield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fa9c9f61f32044c98a357e147565c601
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05714487

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes