Trimethyl orthobeznoate → Tert-butyl 4-oxo-2-phenyl-1,3,8-triazaspiro[4.5]dec-1-ene-8-carboxylate

HRID 1442913Notes

Reaction equation

HRID 1442913 reaction equation
[NH2:1][C:2]1([C:15]([NH2:17])=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CO[C:20](OC)(OC)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[O:16]=[C:15]1[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]2)[N:1]=[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:17]1

Participants

4

Reactant 2

HCID 69720Trimethyl orthobeznoateHCID 10562199tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate

Product 1

HCID 59165778Tert-butyl 4-oxo-2-phenyl-1,3,8-triazaspiro[4.5]dec-1-ene-8-carboxylateYield 30.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 4-amino-4-(aminocarbonyl)piperidine-1-carboxylate (120 mg, 0.493 mmol) and trimethyl orthobenzoate (198 mg, 1.09 mmol) in toluene (7 mL) was heated at 110° C. for 18 h. The reaction was concentrated and the crude product was purified by silica gel chromatography, eluting with a gradient of 0 to 5% methanol:dichloromethane to give the title compound (50 mg). MS: m/z=330.2 (M+1).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude product was purified by silica gel chromatography
  3. washeluting with a gradient of 0 to 5% methanol

Sources & evidence

ORD record
ord-75473b55201a45f0b5d45c1d68defe70
Source dataset
uspto-grants-2010_02
Patent number
US07659264B2

Reaction notes

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