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Acetic Acid → tert-Butyl 9-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-azaspiro[5.5]undecane-3-carboxylate

HRID 1253708
ノート
印刷プレビュー

反応式

HRID 1253708 の反応式
C(O)(=O)C.O=[C:6]1[CH2:23][CH2:22][C:9]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:8][CH2:7]1.[N:24]1[CH:25]=[N:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][C:28]=12.[Na]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[N:24]1[CH:25]=[N:26][N:27]2[CH2:32][CH2:31][N:30]([CH:6]3[CH2:23][CH2:22][C:9]4([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]4)[CH2:8][CH2:7]3)[CH2:29][C:28]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 184069195H,6H,7H,8H-(1,2,4)triazolo(1,5-a)pyrazineHCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

生成物 1

HCID 66701117tert-Butyl 9-(5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-yl)-3-azaspiro[5.5]undecane-3-carboxylate収率 62%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
2 回
HCID 516892Sodium Bicarbonate溶媒

実験手順

Acetic acid (2.34 eq.) was added to a solution of tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (1.122 mmol, 1 eq.) and 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine (1.14 eq.) in methylene chloride (7 ml). Sodium triacetoxyborhydride (1.4 eq) was then added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride and sat. NaHCO3 solution. The aqueous phase was washed with methylene chloride (2×20 ml), and the combined organic phases were dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (silica, ethyl acetate/ethanol 10:1) to obtain the desired product. Yield: 62%

後処理

  1. washThe aqueous phase was washed with methylene chloride (2×20 ml)
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (silica, ethyl acetate/ethanol 10:1)

出典と根拠

ORDレコード
ord-14a9f0001dd04364973ca7fee12507fb
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08455475B2

反応ノート

読み込み中…

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