1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-butyl 4-(cyanomethyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

HRID 1876845Notes

Reaction equation

HRID 1876845 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[C:15]([CH:17]=[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)#[N:16].N12CCCN=C1CCCCC2>C(#N)C>[C:15]([CH2:17][C:18]1([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]1)#[N:16]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 15326949tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate

Product 1

HCID 68755373tert-butyl 4-(cyanomethyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylateYield 61.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (4.3 g, 0.022 mol) in acetonitrile (50 mL) was added tert-butyl 4-(cyanomethylene)piperidine-1-carboxylate (4.9 g, 0.022 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (3.3 mL, 0.022 mol). The resulting mixture was stirred at room temperature overnight. After being evaporated to dryness, the residue was purified on silica gel, eluting with 0-100% EtOAc in hexanes, to give the desired product (5.62 g, 61%). LCMS (M+H) 417.1.

Workup

  1. customAfter being evaporated to dryness
  2. customthe residue was purified on silica gel
  3. washeluting with 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-52af9a42a5eb45698ac32b962592a9b8
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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