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2-Fluoropyridine → tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-(2-pyridinyloxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate

HRID 456770
Notes
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Reaction equation

HRID 456770 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([OH:17])[CH2:14]2)[N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:9])#[N:2].F[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([O:17][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:14]2)[N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:9])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 86598896tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 86598922tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-(2-pyridinyloxy)-2-azabicyclo[2.2.1]heptane-2-carboxylateYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 5-7 (209 mg) in dimethylformamide (2.5ml), were added 2-fluoropyridine (109 mg) and sodium hydride (60% in mineral oil, 25 mg). The mixture was then stirred at room temperature for 50 minutes. The reaction mixture was diluted with ethyl acetate, and washed successively with water and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (162 mg).

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-ab1b2bb05e584f80af9bf862cedfc35a
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07186731B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes