Methanesulfonic Acid → (3R)-3-(2,6-Dichloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one

HRID 1013823ノート

反応式

HRID 1013823 の反応式
C([O:8][C:9]1[CH:30]=[C:29]([Cl:31])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:27][C:26]4[NH:25][N:24]=[CH:23][C:22]=4[CH2:21][CH2:20]3)[C:15]2=[O:28])=[C:11]([Cl:32])[CH:10]=1)C1C=CC=CC=1.CS(O)(=O)=O>CSC>[Cl:32][C:11]1[CH:10]=[C:9]([OH:8])[CH:30]=[C:29]([Cl:31])[C:12]=1[CH2:13][C@@H:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:27][C:26]3[NH:25][N:24]=[CH:23][C:22]=3[CH2:21][CH2:20]2)[C:15]1=[O:28]

参加物

4

反応物 2

HCID 6395Methanesulfonic AcidHCID 67317121(3R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one

生成物 1

HCID 67316410(3R)-3-(2,6-Dichloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one収率 113.2%

試薬・触媒・溶媒 1

HCID 1068Dimethyl Sulfide溶媒

実験手順

To a solution of (3R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-indazol-6-yl)-pyrrolidin-2-one (3.93 g, 8.36 mmol) in dimethylsulfide (45 mL), add methane sulfonic acid (13.23 g, 138 mmol) and stir the mixture vigorously under nitrogen atmosphere at room temperature for 18 hours. Remove the solvent in vacuo and dilute the residue with water, adjust the pH to pH=7 with 5 N NaOH, and extract the mixture several times with ethyl acetate and THF. After drying the combined organic layer (Na2SO4), filter and concentrate under vacuum to afford 3.60 g (100%) of the title compound. MS (m/z): 381 (M+).

後処理

  1. customRemove the solvent in vacuo
  2. additiondilute the residue with water
  3. extractionextract the mixture several times with ethyl acetate and THF
  4. dry with materialAfter drying the combined organic layer (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate under vacuum

出典と根拠

ORDレコード
ord-189297764f9c4b8c93027942d8f3fb8c
出典データセット
uspto-grants-2011_07
特許番号
US07981918B2

反応ノート

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