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

HRID 344022노트

반응식

HRID 344022 반응식
[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]

참가 물질

7

반응물 5

HCID 7841Allyl bromide2회HCID 24758Sodium hydride2회HCID 25517Ammonium ChlorideHCID 3541750tert-butyl N-(2-phenylethyl)carbamateHCID 178418361HCID 178418361, 화합물2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-53edee12b4dc46d8a7c175ac1003615f
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864045

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