Sodium hydride → Ethyl 5-[8-(t-Butoxycarbonyl)-4-keto-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl]pentanoate

HRID 975782노트

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HRID 975782 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][NH:13][C:12]2=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][N:13]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:12]2=[O:22])[CH2:23][CH2:24]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 389488tert-Butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

생성물 1

HCID 67722997Ethyl 5-[8-(t-Butoxycarbonyl)-4-keto-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl]pentanoate수율 75.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a stirred solution of 2.3 g (6.95 mmol) of 8-(t-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one in 40 ml of dry dimethylformamide at 0° C. was added 0.4 g (13 mmol) of sodium hydride (80% in mineral oil). The mixture was stirred at 0° C. under argon for 30 minutes and then ethyl 5-bromopentanoate (2.09 g, 10 mmol) was added dropwise. After being allowed to come to ambient temperature, the mixture was stirred for an additional 20 hours. The mixture was quenched with aqueous ammonium chloride, diluted with water and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium surf ate and concentrated. The residue was purified by column chromatography (silica gel, 0-25% gradient of ethyl acetate in hexane) to provide 2.4 g (75.2%) of the indicated ester as a colorless liquid.

후처리

  1. customto come to ambient temperature
  2. stirringthe mixture was stirred for an additional 20 hours
  3. customThe mixture was quenched with aqueous ammonium chloride
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. dry with materialdried over magnesium
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel, 0-25% gradient of ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-c9c4d599922640048035aecf5d9924c5
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610142

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