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

HRID 1915118노트

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HRID 1915118 반응식
[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]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58026283HCID 58026283, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 21926011acetic acid N,N-dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b15bf576193e4a83853514bb99f62c0d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614323B2

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