Allyl bromide → N-allyl-N-phenethylcarbamic acid tert-butyl ester

HRID 344022ノート

反応式

HRID 344022 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].[CH2:21](Br)[CH:22]=[CH2:23].[Cl-].[NH4+]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:23][CH:22]=[CH2:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 7841Allyl bromide2 回HCID 24758Sodium hydride2 回HCID 25517Ammonium ChlorideHCID 3541750tert-butyl N-(2-phenylethyl)carbamateHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 53637355N-allyl-N-phenethylcarbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Combine N-t-butoxycarbonyl-2-phenyl-ethylamine (22.1 g, 100 mmol) and THF (100 mL) under an inert atmosphere. Cool to 0° C. in an ice-bath. Add portionwise sodium hydride (0.206 g, 110 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (9.50 mL, 110 mmol) and warm to ambient temperature. Cool again to 0° C. in an ice-bath. Add sodium hydride (0.92 g, 40 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (3.0 mL, 35.0 mmol) and heat to reflux for 18 hours. Cool to ambient temperature. Add a saturated aqueous solution of ammonium chloride (200 mL) and extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane to give the title compound.

後処理

  1. temperatureCool again to 0° C. in an ice-bath
  2. temperatureto reflux for 18 hours
  3. temperatureCool to ambient temperature
  4. extractionextract with ethyl acetate
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. washChromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-53edee12b4dc46d8a7c175ac1003615f
出典データセット
uspto-grants-1999_01
特許番号
US05864045

反応ノート

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