tert-butyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate → (2S)-Tert-butyl 4-allyl-4-hydroxy-2-methylpiperidine-1-carboxylate

HRID 403506ノート

反応式

HRID 403506 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C@@H:9]1[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([Mg]Br)[CH:17]=[CH2:18]>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][CH:17]=[CH2:16])([OH:14])[CH2:10][C@@H:9]1[CH3:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 11401606tert-butyl (2S)-2-methyl-4-oxopiperidine-1-carboxylateHCID 178455850HCID 178455850、化合物

生成物 1

HCID 68379051(2S)-Tert-butyl 4-allyl-4-hydroxy-2-methylpiperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

In a argon flushed dry 25 ml 2-neckoundbottomflask (S)-2-methyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (34) (0.6 g, 2.81 mmol) was dissolved in 10 ml of ether. A 1M solution of allylmagnesiumbromide in Et2O (3.66 ml, 3.66 mmol) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 2 h. The mixture was quenched with NH4Cl solution and extracted with ether. The organic layer was washed with brine, dried over Na2 SO4 and evaporated. The crude product was purified by flash chromatography (silica gel, 20-30% EtOAc/cyclohexane) which furnished the product as white solid

後処理

  1. customIn a argon flushed
  2. customThe mixture was quenched with NH4Cl solution
  3. extractionextracted with ether
  4. washThe organic layer was washed with brine
  5. customdried over Na2 SO4
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (silica gel, 20-30% EtOAc/cyclohexane) which

出典と根拠

ORDレコード
ord-821fde4c95414ddb8f3cf416e7d0b7fa
出典データセット
uspto-grants-2014_06
特許番号
US08748435B2

反応ノート

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