Boron trifluoride → HCID 11211410, compound

HRID 2203716Notes

Reaction equation

HRID 2203716 reaction equation
B(F)(F)[F:2].[CH2:5]([O:7][P:8]([N:13]1[CH:19]2[CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:18]2)([O:10][CH2:11][CH3:12])=[O:9])[CH3:6]>C(Cl)Cl>[CH2:5]([O:7][P:8]([NH:13][C@H:19]1[C@H:14]([F:2])[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:18]1)([O:10][CH2:11][CH3:12])=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 6356Boron trifluorideHCID 59455678Benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate

Product 1

HCID 11211410HCID 11211410, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BF3 etherate (3.10 mL, 24.4 mmol) was added to a solution of benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate (3.00 g, 8.14 mmol; Example H, step D) in DCM (10 mL) at 0° C. The resulting solution was warmed to room temperature and stirred at room temperature for 3 days. The solvent was removed in vacuo, ethyl acetate (30 mL) and saturated sodium bicarbonate (20 mL) were added. The organic layer was separated, dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by flash chromatography on silica gel (ethyl acetate) to give trans-benzyl 3-(diethoxyphosphorylamino)-4-fluoropiperidine-1-carboxylate (0.53 g, 17%) as oil.

Workup

  1. customThe solvent was removed in vacuo, ethyl acetate (30 mL) and saturated sodium bicarbonate (20 mL)
  2. additionwere added
  3. customThe organic layer was separated
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified by flash chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-306eb9e100e54594808ed05745909b9c
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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