Sodium hydride → 9-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

HRID 16222

反応式

HRID 16222 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:14][CH:13]2[CH:15]([N:16]3[CH2:20][CH:19]([CH2:21][OH:22])[C:18]([CH3:24])([CH3:23])[C:17]3=[O:25])[CH:9]([CH2:10][CH2:11][CH2:12]2)[CH2:8]1)=[O:6].Cl[C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=1>O1CCCC1.CN1CCCN(C)C1=O>[CH3:3][O:4][C:5]([CH:7]1[CH2:14][CH:13]2[CH:15]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][C:27]4[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][N:28]=4)[C:18]([CH3:23])([CH3:24])[C:17]3=[O:25])[CH:9]([CH2:10][CH2:11][CH2:12]2)[CH2:8]1)=[O:6]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 666569529-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

生成物 1

HCID 666569249-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

実験手順

NaH (0.1 g, 60% in oil, 2.56 mmol) was added in one portion to a stirred and cooled (0° C.) solution of the product of Example 7D (0.48 g, 1.42 mmol) and 6-chloro-nicotinonitrile (0.35 g, 2.56 mmol) in tetrahydrofuran (7 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL). After the addition, the solution was warmed to room temperature and stirred for another five hours. The dark brown reaction mixture was cooled (0° C.), quenched with acetic acid (0.1 mL), and partitioned with diethyl ether and water. The organic phase was washed with water and brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 5-80% ethyl acetate in hexanes to give the titled product as a solid.

後処理

  1. additionAfter the addition
  2. stirringstirred for another five hours
  3. temperatureThe dark brown reaction mixture was cooled (0° C.)
  4. customquenched with acetic acid (0.1 mL)
  5. custompartitioned with diethyl ether and water
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified over silica gel using 5-80% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-12166c3d0fd24dd2a46056d22bd7f91a
出典データセット
uspto-grants-2010_06
特許番号
US07737137B2

関連ノート

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