Acetonitrile → (S)-1-(2-(5-((Dimethylamino)methyl)isoxazol-3-yl)pyrrolidin-1-yl)-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone

HRID 710038ノート

反応式

HRID 710038 の反応式
CS(O[CH2:6][C:7]1[O:11][N:10]=[C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:32])[C:18]([F:31])([F:30])[C:19]2([OH:29])[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)[CH:8]=1)(=O)=O.C1COCC1.[CH3:38]COC(C)=O.C[C:45]#[N:46]>>[CH3:38][N:46]([CH2:6][C:7]1[O:11][N:10]=[C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:32])[C:18]([F:30])([F:31])[C:19]2([OH:29])[CH2:24][C:23]([CH3:25])([CH3:26])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)[CH:8]=1)[CH3:45]

参加物

5

反応物 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 86706749(S)-(3-(1-(2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetyl)pyrrolidin-2-yl)isoxazol-5-yl)methyl methanesulfonate

生成物 1

HCID 73672156(S)-1-(2-(5-((Dimethylamino)methyl)isoxazol-3-yl)pyrrolidin-1-yl)-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone

実験手順

The compound (160 mg) obtained in Example 3-(5) was dissolved in MeCN and after adding a THF solution of dimethyllamine (2 M, 250 μL), the mixture was stirred at room temperature for 3 hours. To the reaction mixture, AcOEt (50 ml) and a saturated aqueous solution of NaCO3 (50 ml) were added to separate the organic layer. The resulting organic layer was washed with brine (50 ml), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (83 mg, colorless amorphous.)

後処理

  1. customto separate the organic layer
  2. washThe resulting organic layer was washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas further purified by silica gel chromatography (AcOEt/hexane)

出典と根拠

ORDレコード
ord-6bcebc64d7a64470aa40ec0ac8e1962a
出典データセット
uspto-grants-2015_11
特許番号
US09181229B2

反応ノート

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