Diisopropylethylamine → HCID 86709525, compound

HRID 1848533Notes

Reaction equation

HRID 1848533 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[C:4](=[O:12])[N:3]1[C:13]1[CH2:14][O:15][C:16](=[O:18])[CH:17]=1.C(N(C(C)C)CC)(C)C.[CH3:28][C:29]1[C:37]([C@@H:38]2[CH2:40][O:39]2)=[CH:36][CH:35]=[C:34]2[C:30]=1[CH2:31][O:32][C:33]2=[O:41]>C(O)C>[OH:39][C@H:38]([C:37]1[C:29]([CH3:28])=[C:30]2[C:34](=[CH:35][CH:36]=1)[C:33](=[O:41])[O:32][CH2:31]2)[CH2:40][N:9]1[CH2:8][CH2:7][C:5]2([C:4](=[O:12])[N:3]([C:13]3[CH2:14][O:15][C:16](=[O:18])[CH:17]=3)[CH:2]([CH3:1])[CH2:6]2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 867094583-Methyl-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 86709525HCID 86709525, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Methyl-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-22, 0.257 mmol) was dissolved in ethanol (3 mL), and treated with diisopropylethylamine (135 μl, 0.771 mmol) followed by (R)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one (I-4B, 73.3 mg, 0.385 mmol). The mixture was heated at 80° C. in a sealed tube for 12 hours. The reaction mixture was then cooled to room temperature and concentrated. The resulting crude product was purified by column chromatography eluting with a 0-20% MeOH/EtOAc gradient to give the title product as a mixture of diastereomers. LC-MS (IE, m/z): 441.3 (M+1)+.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated
  3. customThe resulting crude product was purified by column chromatography
  4. washeluting with a 0-20% MeOH/EtOAc gradient

Sources & evidence

ORD record
ord-495d64835a354bc193fc7e31b2179159
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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