Cyclobutanone → (6-Chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone

HRID 404546ノート

反応式

HRID 404546 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:17]1(=O)[CH2:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 14496CyclobutanoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 509999191-[(6-Chloropyridin-3-yl)carbonyl]-1,4-diazepane

生成物 1

HCID 58076653(6-Chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

To a solution of (6-chloro-pyridin-3-yl)[1,4]diazepan-1-yl-methanone (255.1 g, 1.06 mol) in dichloroethane (3.0 L) was added cyclobutanone (108.1 mL, 1.45 mol). After a 1 h aging period, sodium triacetoxyborohydride (308.2 g, 1.45 mol) was added in four equal portions over 1.5 h. The resulting mixture was allowed to stir for 20 h, then quenched with 2.5 L of an aqueous solution containing NaOH (141.3 g, 3.53 mol). After stirring for 30 minutes, the layers were separated and the organic dried with magnesium sulfate, filtered, and concentrated to yield the title compound as an oil.

後処理

  1. customquenched with 2.5 L of an aqueous solution
  2. stirringAfter stirring for 30 minutes
  3. customthe layers were separated
  4. dry with materialthe organic dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c4f23b62bd9149b79cfd132d752d3ed9
出典データセット
uspto-grants-2014_06
特許番号
US08748596B2

反応ノート

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