Ethyl Acetate → Benzyl 3-bromopropylcarbamate

HRID 1509362

反応式

HRID 1509362 の反応式
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

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 787013-Bromopropylamine hydrobromide

生成物 1

HCID 254436Benzyl 3-bromopropylcarbamate収率 100%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-653ead481aa744f39f7571dd4fd9be26
出典データセット
uspto-grants-2015_12
特許番号
US09222941B2

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