Methanol → HCID 12046883, compound

HRID 2203708Notes

Reaction equation

HRID 2203708 reaction equation
B(F)(F)F.[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].[CH3:30][OH:31]>>[CH2:5]([O:7][P:8]([NH:13][C@H:19]1[C@H:14]([O:31][CH3:30])[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 3

HCID 887MethanolHCID 6356Boron trifluorideHCID 59455678Benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate

Product 1

HCID 12046883HCID 12046883, compoundYield 94%

Conditions

Temperature
0 °C

Procedure

BF3 etherate (1.35 mL, 10.6 mmol) was added to a solution of benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate (1.96 g, 5.32 mmol) in methanol (10 mL) at 0° C. and stirred at 0° C. for 2 hours. 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 to give trans-benzyl 3-(diethoxyphosphorylamino)-4-methoxypiperidine-1-carboxylate (2.00 g, 94%) as an 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

Sources & evidence

ORD record
ord-9817441e27d94b34993e6d83196cf72f
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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