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Ethanol → 8-[2-(Methylamino)-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 1501850
ノート
印刷プレビュー

反応式

HRID 1501850 の反応式
[CH3:1][C:2]1[C:10]([C:11](=O)[CH2:12][N:13]2[CH2:30][CH2:29][C:16]3([C:20](=[O:21])[N:19]([C:22]4[CH2:23][O:24][C:25](=[O:28])[C:26]=4[CH3:27])[CH2:18][CH2:17]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:32].[CH3:33][NH2:34].CCO.[BH4-].[Na+]>C1COCC1>[CH3:33][NH:34][CH:11]([C:10]1[CH:9]=[CH:8][C:7]2[C:6](=[O:32])[O:5][CH2:4][C:3]=2[C:2]=1[CH3:1])[CH2:12][N:13]1[CH2:14][CH2:15][C:16]2([C:20](=[O:21])[N:19]([C:22]3[CH2:23][O:24][C:25](=[O:28])[C:26]=3[CH3:27])[CH2:18][CH2:17]2)[CH2:29][CH2:30]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 702EthanolHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 867095278-(2-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

生成物 1

HCID 729486488-[2-(Methylamino)-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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 8-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (25 mg, 0.057 mmol) and methyl amine (4 mg, 0.114 mmol) in anhydrous THF was added Ti(O-iPr)4(35 μL, 0.114 mmol). The reaction was sealed and shaken at ambient temperature for 16 hr. To this reaction, EtOH (200 proof, 0.5 mL) was added followed by adding NaBH4 (11 mg, 0.171 mmol) portion-wise within 30 min. The reaction was shaken for 3 hr and quenched with water (0.5 mL). The reaction was partitioned between EtOAc (4 mL×2) and ammonium (2N, 1.5 mL). The organic phase was combined and evaporated under reduced pressure. The residue was dissolved in DMSO (1.5 mL) and filtered. The crude product was purified by using reversed-phase HPLC (Acetonitrile with 0.1% TFA: water with 0.1% TFA from 10% to 60%) to give the title compound. LC-MS (IE, m/z): 454 [M+1]+.

後処理

  1. customThe reaction was sealed
  2. additionwas added
  3. stirringThe reaction was shaken for 3 hr
  4. customquenched with water (0.5 mL)
  5. customThe reaction was partitioned between EtOAc (4 mL×2) and ammonium (2N, 1.5 mL)
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in DMSO (1.5 mL)
  8. filtrationfiltered
  9. customThe crude product was purified

出典と根拠

ORDレコード
ord-b5fdbdf1d688417da4d3872de03d0830
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206198B2

反応ノート

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