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

HRID 975782ノート

反応式

HRID 975782 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c9c4d599922640048035aecf5d9924c5
出典データセット
uspto-grants-1997_03
特許番号
US05610142

反応ノート

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