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

HRID 324523

反応式

HRID 324523 の反応式
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]

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 5767401H-Benzotriazole-1-carboxaldehyde2 回HCID 22253999tert-butyl N-[4-(isopropylamino)cyclohexyl]methylcarbamate

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f7081003ac540b9890b293ca19f9d7b
出典データセット
uspto-grants-2001_04
特許番号
US06218408B1

関連ノート

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