Water → 2,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-[(4-bromophenyl)methyl]-1-oxo-, 1,1-dimethylethyl ester

HRID 1182157노트

반응식

HRID 1182157 반응식
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:20][CH2:19][C:13]2([C:17](=[O:18])[NH:16][CH2:15][CH2:14]2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.O>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][C:13]2([C:17](=[O:18])[N:16]([CH2:26][C:25]3[CH:28]=[CH:29][C:22]([Br:21])=[CH:23][CH:24]=3)[CH2:15][CH2:14]2)[CH2:19][CH2:20]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 45073946tert-Butyl 1-oxo-2,8-diazaspiro(4.5)decane-8-carboxylate

생성물 1

HCID 589819962,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-[(4-bromophenyl)methyl]-1-oxo-, 1,1-dimethylethyl ester수율 111.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

Introduce 600 mg (14.7 mmol) of sodium hydride (60% suspension in mineral oil) in a 500 mL round bottom flask under nitrogen before adding successively 20 mL of anhydrous DMF and 2.5 g (9.8 mmol) of 1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester previously dissolved in 20 mL of anhydrous DMF. After agitating one hour at room temperature, 2.5 g (9.8 mmol) of 4-bromobenzylbromide diluted in 20 mL of anhydrous DMF were added and the reaction mixture was agitated an additional hour at room temperature. Then 100 mL of water were added and the solution was extracted with diethyl ether (2×150 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated under reduced pressure to yield 4.63 g of 2-(4-bromobenzyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester as a yellow oil.

후처리

  1. additionwere added
  2. stirringthe reaction mixture was agitated an additional hour at room temperature
  3. extractionthe solution was extracted with diethyl ether (2×150 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-8f926eaf6eec441dbc9e2502f8b92387
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288548B2

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