Triethylamine → 6-(2,4-Dichloro-benzylcarbamoyl)-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester

HRID 2407529Notes

Reaction equation

HRID 2407529 reaction equation
C(O)(=O)C(O)=O.[C:7]([O:11][C:12]([N:14]1[CH2:20][C:16]2([CH2:19][NH:18][CH2:17]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[Cl:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=1[CH2:36][N:37]=[C:38]=[O:39]>ClCCl>[C:7]([O:11][C:12]([N:14]1[CH2:15][C:16]2([CH2:17][N:18]([C:38](=[O:39])[NH:37][CH2:36][C:30]3[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:29]=3[Cl:28])[CH2:19]2)[CH2:20]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46127082,4-Dichlorobenzyl isocyanateHCID 53350400tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate oxalate

Product 1

HCID 866823436-(2,4-Dichloro-benzylcarbamoyl)-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl esterYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(tert-butoxycarbonyl)-2,6-diaza-spiro[3.3]heptane oxalate (200 mg, 1.01 mmol) in dichloromethane (10 mL) was added triethylamine (141 μl, 1.01 mmol) followed by 2,4-dichloro-1-(isocyanatomethyl)benzene (204 mg, 1.01 mmol). The reaction mixture was stirred at ambient temperature for 1 h. The crude reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography (SiO2; methanol:dichloromethane 0:1 to 1:9) to give the title compound (344 mg, 85%) as a white solid. MS (EI) m/e: 400.0 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by chromatography (SiO2; methanol:dichloromethane 0:1 to 1:9)

Sources & evidence

ORD record
ord-ed61985dd540493db176fb4a46aaea7f
Source dataset
uspto-grants-2014_08
Patent number
US08809552B2

Reaction notes

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