Sodium Hydroxide → 2-[4-(Diethoxymethyl)benzyl]-8-isobutyl-2,8-diazaspiro[4.5]decane

HRID 2067721ノート

反応式

HRID 2067721 の反応式
[CH2:1]([N:5]1[CH2:14][CH2:13][C:8]2([CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].[CH2:15]([O:17][CH:18]([O:27][CH2:28][CH3:29])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.CN(C)C=O>[CH2:28]([O:27][CH:18]([O:17][CH2:15][CH3:16])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:11]2[CH2:10][CH2:9][C:8]3([CH2:7][CH2:6][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:14][CH2:13]3)[CH2:12]2)=[CH:21][CH:20]=1)[CH3:29]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58026283HCID 58026283、化合物

生成物 1

HCID 689535472-[4-(Diethoxymethyl)benzyl]-8-isobutyl-2,8-diazaspiro[4.5]decane収率 61.5%

試薬・触媒・溶媒 1

HCID 21926011acetic acid N,N-dimethylformamide溶媒

実験手順

To a 10% acetic acid-dimethylformamide (10 mL) solution of 8-isobutyl-2,8-diazaspiro[4.5]decane (600 mg) and 4-(diethoxymethyl)benzaldehyde (661 mg), sodium triacetoxyborohydride (1.30 g) was added. The reaction solution was stirred at room temperature for 14 hours. To the reaction solution, an aqueous 5N sodium hydroxide solution (10 mL) was added. The aqueous layer was extracted twice with dichloromethane (20 mL). The combined organic layer was washed with saturated sodium chloride solution (20 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 (ethyl acetate:methanol: 28% aqueous ammonia=1:0:0→100:5:1→100:10:2) to obtain the title compound (730 mg) having the following physical properties.

後処理

  1. extractionThe aqueous layer was extracted twice with dichloromethane (20 mL)
  2. washThe combined organic layer was washed with saturated sodium chloride solution (20 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 (ethyl acetate:methanol: 28% aqueous ammonia=1:0:0→100:5:1→100:10:2)

出典と根拠

ORDレコード
ord-9f6d769491ca43cfa9de24b345e726c4
出典データセット
uspto-grants-2012_10
特許番号
US08293896B2

反応ノート

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