Ethyl Acetate → Benzyl 3-bromopropylcarbamate

HRID 1509362

반응식

HRID 1509362 반응식
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].C(OCC)(=O)C>[OH-].[Na+]>[CH2:11]([O:10][C:8]([NH:6][CH2:5][CH2:4][CH2:3][Br:2])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 787013-Bromopropylamine hydrobromide

생성물 1

HCID 254436Benzyl 3-bromopropylcarbamate수율 100%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

3-Bromopropylamine hydrobromide (5.0 g, 22.8 mmol) was dissolved in an aqueous NaOH solution (15 wt %, 80 ml) and cooled to 0° C. under nitrogen before benzyl chloroformate was added dropwise. The reaction was left to stir overnight then ethyl acetate (100 ml) was added and the phases were separated. The organic phase was further washed with a HCl solution (2 M, 100 ml), a NaOH solution (2 M, 100 ml), brine (100 ml), dried over Na2SO4, and evaporated to yield 12 as a clear oil (6.22 g, 22.8 mmol, 100%). Rf=0.31 (8:2 Hexane/Ethyl acetate); 1H NMR (300 MHz, CDCl3) δ=7.40-7.33 (m, 5H, ArCH), 5.11 (s, 2H, CH2Ph), 4.94 (bs, 1H, NHCbz), 3.45 (t, 3J(H,H)=6.4 Hz, 2H, CH2Br), 3.36 (q, 3J(H,H)=6.4 Hz, 2H, CH2NHCbz), 2.08 (q, 3J(H,H)=6.4 Hz, 2H, CH2CH2CH2); 13C NMR (75 MHz, CDCl3) δ=156.4 (CO), 136.4 (ArCCH2), 128.5 (ArCH), 128.2 (ArCH), 127.0 (ArCH), 66.8 (CH2Ph), 39.4 (CH2NHCbz), 32.4 (CH2CH2CH2), 30.6 (CH2Br); HRMS (ESI+): m/z calculated for C11H14BrNO2Na [M+Na]+: 294.0106, found 294.0099.

후처리

  1. additionwas added dropwise
  2. waitThe reaction was left
  3. customthe phases were separated
  4. washThe organic phase was further washed with a HCl solution (2 M, 100 ml)
  5. dry with materiala NaOH solution (2 M, 100 ml), brine (100 ml), dried over Na2SO4
  6. customevaporated

출처 및 근거

ORD 기록
ord-653ead481aa744f39f7571dd4fd9be26
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09222941B2

연결된 노트

불러오는 중…