Dichloromethane methanol → (R)-methyl 6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoate

HRID 885515Notes

Reaction equation

HRID 885515 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([N:16]=[N+:17]=[N-:18])[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[CH3:21].Cl[CH2:23]Cl.CO>C[Si](C=[N+]=[N-])(C)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([N:16]=[N+:17]=[N-:18])[C:13]([O:15][CH3:23])=[O:14])=[CH:4][C:3]=1[CH3:21]

Participants

4

Reactant 2

HCID 21226129Dichloromethane methanolHCID 86667070(R)-6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoic acid

Product 1

HCID 86667072(R)-methyl 6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoateYield 83%

Reagents, catalysts & solvents 1

HCID 167693TrimethylsilyldiazomethaneSolvent

Procedure

To a solution of crude (R)-6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoic acid (0.163 g, 0.552 mmol) in 10 mL of dichloromethane/methanol (4:1), trimethylsilyldiazomethane was added dropwise until the solution became yellow. After stirred at room temperature under N2 for 30 min, the reaction mixture was concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-100% dichloromethane/hexanes to give the title compound as colorless oil (0.141 g, 83% yield)

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe product was isolated by Flash column chromatography (silica gel column)
  3. washeluting with 0-100% dichloromethane/hexanes

Sources & evidence

ORD record
ord-1d56054f55494af887f945960f4ef23d
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

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