Tetrahydrofuran → tert-butyl N-[4-(isopropylformylamino)cyclohexyl]-methyl-carbamate

HRID 324523

반응식

HRID 324523 반응식
C(NC1CCC([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])CC1)(C)C.[N:20]1([CH:29]=[O:30])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.[CH2:31]1[CH2:35]OC[CH2:32]1>>[CH:31]([C:29]([NH:20][CH:24]1[CH2:25][CH2:26][CH:27]([N:12]([CH3:11])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:28][CH2:23]1)=[O:30])([CH3:35])[CH3:32]

참가 물질

4

반응물 3

HCID 8028Tetrahydrofuran2회HCID 5767401H-Benzotriazole-1-carboxaldehyde2회HCID 22253999tert-butyl N-[4-(isopropylamino)cyclohexyl]methylcarbamate

생성물 1

HCID 69323481tert-butyl N-[4-(isopropylformylamino)cyclohexyl]-methyl-carbamate수율 100%

실험 절차

A solution of a tert-butyl N-[4-(isopropylamino)-cyclohexyl]methylcarbamate (7.89 mmol, 1 equivalent) in 5 ml of THF was added dropwise to a solution of 1H-benzotriazole-1-carboxaldehyde (8.68 mmol, 1.2 equivalents) in 10 ml of THF at room temperature. The reaction mixture was stirred overnight and heated at reflux temperature for two hours. 1H-benzotriazole-1-carboxaldehyde (additional 1 equivalent) was added to the reaction mixture and stirred overnight. The solvent was removed and dichloromethane was added to the residue. The organic phase was washed with 2N NaOH solution, saturated with NaCl solution, dried over Na2SO4, the solvent removed, and the residue chromatographed to give tert-butyl N-[4-(isopropylformylamino)cyclohexyl]-methyl-carbamate: 100% yield, 299 (ESMS, MH+); 1H NMR (CD3OD) δ 8.22 & 8.18 (two s, 1H), 4.63 (broad, 1H), 4.30 & 3.60 (two m, 1H), 3.76 (m, 1H), 2.99 (m, 2H), 1.44 (s, 9H), 1.27 (d, 3H, J=6.5 Hz), 1.21 (d, 3H, J=6.5 Hz), 1.91-0.82 (m, 9H).

후처리

  1. temperatureheated
  2. temperatureat reflux temperature for two hours
  3. stirringstirred overnight
  4. customThe solvent was removed
  5. additiondichloromethane was added to the residue
  6. washThe organic phase was washed with 2N NaOH solution, saturated with NaCl solution
  7. dry with materialdried over Na2SO4
  8. customthe solvent removed
  9. customthe residue chromatographed

출처 및 근거

ORD 기록
ord-4f7081003ac540b9890b293ca19f9d7b
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218408B1

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