Sodium Hydroxide → Tert-butyl 8-[(3-methyl-2-thienyl)methyl]-2,8-diazaspiro[4.5]decane-2-carboxylate

HRID 2067719

반응식

HRID 2067719 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 68952905Tert-butyl 8-[(3-methyl-2-thienyl)methyl]-2,8-diazaspiro[4.5]decane-2-carboxylate수율 61.1%

시약·촉매·용매 1

HCID 21926011acetic acid N,N-dimethylformamide용매

실험 절차

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-carboaldehyde (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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b21f8056ee634d2da4d2f47d8a17a02f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293896B2

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