N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutane → N-(3-aminopropyl)-N-(tert-butoxycarbonyl)-N',N'-dimethyl-1,4-diaminobutane

HRID 1683312노트

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HRID 1683312 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12]([N:14]([CH2:22][CH2:23][C:24]#[N:25])[CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[O:13])([CH3:10])([CH3:9])[CH3:8]>CCOCC>[NH2:25][CH2:24][CH2:23][CH2:22][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH3:20])[CH3:21]

참가 물질

4

반응물 2

HCID 19695906N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutaneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 18934679N-(3-aminopropyl)-N-(tert-butoxycarbonyl)-N',N'-dimethyl-1,4-diaminobutane수율 59%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

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온도
0 °C

실험 절차

To a solution of LAH (0.62 mg, 16.30 mmol) in anhydrous ether (100 ml) was added N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutane 324 (2.22 g, 8.10 mmol) in anhydrous ether (50 ml) at 0° C. The mixture was stirred at 0° C. for thirty minutes. The excess LAH was quenched with 1N NaOH at 0° C., and the resulting suspension was filtered through Celite and washed with ether. The combined ether layers were washed with brine, dried over MgSO4, and concentrated in vacuo to yield a crude product. The crude product was purified on a flash silica gel column and eluted with chloroform:methanol:isopropylamine (15:1:1) to give N-(3-aminopropyl)-N-(tert-butoxycarbonyl)-N',N'-dimethyl-1,4-diaminobutane 325 (1.30 g, 59% yield). 1H NMR (400 MHz, CDCl3) δ: 1.40 (9H, s, t-Bu), 2.15 (6H, s, --N(CH3)2), 2.22 (2H, m), 2.65 (2H, t), 3.20 (4H, m).

후처리

  1. customThe excess LAH was quenched with 1N NaOH at 0° C.
  2. filtrationthe resulting suspension was filtered through Celite
  3. washwashed with ether
  4. washThe combined ether layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto yield a crude product
  8. customThe crude product was purified on a flash silica gel column
  9. washeluted with chloroform:methanol:isopropylamine (15:1:1)

출처 및 근거

ORD 기록
ord-451cdb02803b4d35b1ce86e40bba0bc3
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05637691

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