4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → 8-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848534Notes

Reaction equation

HRID 1848534 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[O:5][CH2:4][C:3]=1[N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]1=[O:18].[CH3:19][C:20]1[C:28]2[CH2:27][O:26][C:25](=[O:29])[C:24]=2[CH:23]=[CH:22][C:21]=1[C@@H:30]1[CH2:32][O:31]1>C(O)C>[OH:31][C@H:30]([C:21]1[CH:22]=[CH:23][C:24]2[C:25](=[O:29])[O:26][CH2:27][C:28]=2[C:20]=1[CH3:19])[CH2:32][N:15]1[CH2:16][CH2:17][C:10]2([C:9](=[O:18])[N:8]([C:3]3[CH2:4][O:5][C:6](=[O:7])[C:2]=3[CH3:1])[CH2:12][CH2:11]2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 867095242-(4-Methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 729500748-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (I-17, 6.00 g, 24.0 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (1-4B, 5.93 g, 31.2 mmol) in ethanol (20 mL) in a sealed tube was heated at 95° C. overnight. After concentration, the residue was purified on silica gel column using methanol/dichloromethane, then precipitated from methanol to give the title compound. LC/MS, (M+1)+: 440.93. 1HNMR (500 MHz, CDCl3), δ7.845-7.809 (m, 2H), 5.290-5.278 (m, 4H), 5.139-5.112 (m, 1H), 4.072-4.044 (t, J=7.1 Hz, 2H), 3.190-3.167 (m, 1H), 2.876-2.859 (m, 1H), 2.636-2.604 (m, 2H), 2.468-2.421 (m, 1H), 2.311 (s, 3H), 2.350-2.328 (m, 1H), 2.193-2.165 (t, J=7.1 Hz, 2H), 2.101-2.039 (m, 5H), 1.668-1.618 (m, 2H).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified on silica gel column
  3. customprecipitated from methanol

Sources & evidence

ORD record
ord-88f27cbbbae7439ebca14bfce2943317
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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