Hydrogen Peroxide → 4-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}thiomorpholine-1-oxide

HRID 272874ノート

反応式

HRID 272874 の反応式
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][N:23]4[CH2:28][CH2:27][S:26][CH2:25][CH2:24]4)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(OO)=[O:32].OO>C(O)(C(F)(F)F)=O.C(Cl)Cl.[OH-].[Na+]>[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([CH2:22][N:23]4[CH2:24][CH2:25][S:26](=[O:32])[CH2:27][CH2:28]4)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

7

反応物 3

HCID 784Hydrogen PeroxideHCID 10290812Trifluoroperacetic acidHCID 598374654-{4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-thiomorpholine

生成物 1

HCID 598374024-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}thiomorpholine-1-oxide収率 79%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒2 回HCID 14798Sodium Hydroxide溶媒

反応条件

温度
7.5 °C

実験手順

To a solution of 4-{4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-ylmethyl}-thiomorpholine (200 mg, 0.494 mmol) in TFA (0.67 ml) at 5 to 10° C. was added dropwise a solution of trifluoro-peracetic acid [4M solution prepared by the addition of 27.5% H2O2 (0.94 ml) to TFA (1.56 ml)] and stirred at 5 to 10° C. for 1 hour. The reaction mixture was diluted with DCM (5 ml) and NaOH (5M solution, 4 ml) was added to attain pH14. The mixture was extracted with DCM ((2×5 ml), the combined DCM extracts were washed with saturated aqueous brine (10 ml), dried over MgSO4, filtered and concentrated in vacuo. The isolated yellow oil was purified by column chromatography on silica eluting with DCM(95):MeOH(4):NH3(I) to give the title compound as a yellow oil (165 mg, 79%). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, 2H), 6.87 (d, 2H), 4.02 (t, 2H), 3.81-3.69 (m, 2H), 3.59-3.43 (m, 2H), 2.99-2.82 (m, 2H), 2.76-2.2.59 (m, 6H), 2.53 (br s, 4H), 2.46 (s, 2H), 2.31-1.73 (m, 12H).

後処理

  1. additionwas added
  2. extractionThe mixture was extracted with DCM ((2×5 ml)
  3. washthe combined DCM extracts were washed with saturated aqueous brine (10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe isolated yellow oil was purified by column chromatography on silica eluting with DCM(95)

出典と根拠

ORDレコード
ord-1d954a6f6e134e37bd26186fbbf05906
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

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