4-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrile → HCID 69224044、化合物

HRID 916320ノート

反応式

HRID 916320 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][Mg]Br.[O:11]=[C:12]1[CH2:18][CH:17]2[N:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([C:30]#[N:31])=[CH:22][CH:21]=3)[CH:14]([CH2:15][CH2:16]2)[CH2:13]1>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][C:12]1([OH:11])[CH2:13][CH:14]2[N:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([C:30]#[N:31])=[CH:22][CH:21]=3)[CH:17]([CH2:16][CH2:15]2)[CH2:18]1

参加物

4

反応物 2

HCID 247436404-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrileHCID 178419673HCID 178419673、化合物

生成物 1

HCID 69224044HCID 69224044、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1,3-Dioxane-2-ylethyl magnesium bromide reagent (0.5 M solution in anhydrous THF: 860 μL, 0.43 mmol) was added dropwise to a solution of 156AF03-217 (80 mg, 0.29 mmol) in anhydrous THF (2 mL) at rt. After 48 h stirring at rt the reaction was quenched with saturated ammonium chloride. The mixture was partitioned between ammonium chloride and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a stepwise gradient of 40-100% ethyl acetate in n-heptane, afforded the desired compound as a diastereomeric mixture, ratio 85:15 (37 mg, 45%).

後処理

  1. customwas quenched with saturated ammonium chloride
  2. customThe mixture was partitioned between ammonium chloride and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the residue by silica gel column chromatography
  7. washeluting with a stepwise gradient of 40-100% ethyl acetate in n-heptane

出典と根拠

ORDレコード
ord-c49b1741b9194d6a9f61f85857724a47
出典データセット
uspto-grants-2007_09
特許番号
US07268232B2

反応ノート

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