Sodium Bicarbonate → HCID 86680070, compound

HRID 1915859Notes

Reaction equation

HRID 1915859 reaction equation
[N:1]([CH:4]1[CH:10](O)[CH2:9][CH2:8][N:7]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:6][CH2:5]1)=[N+:2]=[N-:3].COCCN(S(F)(F)[F:32])CCOC.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[N:1]([CH:4]1[CH:10]([F:32])[CH2:9][CH2:8][N:7]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:6][CH2:5]1)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58076845HCID 58076845, compound

Product 1

HCID 86680070HCID 86680070, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 4-azido-5-hydroxyazepane-1-carboxylate (1.0 g, 3.45 mmol) in dry DCM (10 ml) was added deoxo-Fluor® (1.6 mL, 8.62 mmol, 50% in THF) and the mixture was stirred at room temperature for 18 hr. Saturated aqueous NaHCO3 solution was added (20 mL) and the mixture was extracted with DCM (100 mL). The organic layer was washed with saturated aqueous NaHCO3 solution (20 mL), separated, dried over MgSO4 and concentrated under reduced pressure. The residue was purified via silica gel column chromatography (20% EtOAc/isohexane) to give benzyl 4-azido-5-fluoroazepane-1-carboxylate as a mixture of syn and anti isomers as a pale yellow oil (0.76 g).

Workup

  1. extractionthe mixture was extracted with DCM (100 mL)
  2. washThe organic layer was washed with saturated aqueous NaHCO3 solution (20 mL)
  3. customseparated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via silica gel column chromatography (20% EtOAc/isohexane)

Sources & evidence

ORD record
ord-d53e61c941114c1fa56a87792fe386d0
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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