Water → (R)-3-(3,5-Dichloro-4'-methanesulfonyl-biphenyl-4-ylmethyl)-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one

HRID 1692108ノート

反応式

HRID 1692108 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][Si](C(C)C)(C(C)C)C(C)C)[CH2:16][CH2:15]2)[C:10]1=[O:31].O.C(O)(C(F)(F)F)=O>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:40])=[O:41])=[CH:35][CH:34]=2)[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[C:10]1=[O:31]

参加物

6

反応物 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66905070(R)-3-(3,5-Dichloro-4'-methanesulfonyl-biphenyl-4-ylmethyl)-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one

生成物 1

HCID 57672048(R)-3-(3,5-Dichloro-4'-methanesulfonyl-biphenyl-4-ylmethyl)-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one収率 96.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of (R)-3-(3,5-Dichloro-4′-methanesulfonyl-biphenyl-4-ylmethyl)-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one (0.12 g) in THF (6 mL), add water (6 mL) and TFA (2 mL). Stir the mixture at room temperature for 12 hours. Dilute the reaction mixture with ethyl acetate and wash with sodium bicarbonate (Sat.) and water. Separate the organic and dry over sodium sulfate, filter and concentrate. Purify the crude mixture on silica gel column with 50% ethyl acetate in hexane to 100% ethyl acetate to afford 0.088 g of the titled product. MS (m/z): 497 (M+).

後処理

  1. washwash with sodium bicarbonate (Sat.) and water
  2. customSeparate the organic and
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude mixture on silica gel column with 50% ethyl acetate in hexane to 100% ethyl acetate

出典と根拠

ORDレコード
ord-b57e68bba6f4432b801d0f8741b43fd4
出典データセット
uspto-grants-2012_04
特許番号
US08153807B2

反応ノート

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