Sodium Hydroxide → HCID 68952905、化合物

HRID 539396

反応式

HRID 539396 の反応式
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[CH3:18][C:19]1[CH:23]=[CH:22][S:21][C:20]=1[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.CN(C)C=O>[CH3:18][C:19]1[CH:23]=[CH:22][S:21][C:20]=1[CH2:24][N:8]1[CH2:7][CH2:6][C:5]2([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]2)[CH2:10][CH2:9]1

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 799113-Methyl-2-thiophenecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

生成物 1

HCID 68952905HCID 68952905、化合物収率 61.1%

試薬・触媒・溶媒 1

HCID 21926011acetic acid N,N-dimethylformamide溶媒

実験手順

To a 1% acetic acid-dimethylformamide (10 mL) solution of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (1.28 g) and 3-methylthiophene-2-carbaldehyde (700 mg), sodium triacetoxyborohydride (1.96 g) was added. The reaction solution was stirred at room temperature for 15 hours. To the reaction solution, an aqueous 5N sodium hydroxide solution (10 mL) was added. The aqueous layer was washed twice with dichloromethane (100 mL) The combined organic layer was washed with saturated sodium chloride solution (50 mL) and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1→1:3) to obtain the title compound (1.14 g) having the following physical properties.

後処理

  1. washThe aqueous layer was washed twice with dichloromethane (100 mL) The combined organic layer
  2. washwas washed with saturated sodium chloride solution (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:1→1:3)

出典と根拠

ORDレコード
ord-91c554556952439db2106a03bef9a055
出典データセット
uspto-grants-2014_10
特許番号
US08871210B2

関連ノート

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