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

HRID 917516Notes

Reaction equation

HRID 917516 reaction equation
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]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:28][CH2:23]1)=[O:30])([CH3:35])[CH3:32]

Participants

4

Reactant 3

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

Product 1

HCID 22253966tert-butyl N-[4-(isopropylformylamino)cyclohexyl]methylcarbamateYield 100%

Procedure

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 equivalent) in 10 ml of THF at room temperature. The reaction mixture was stirred overnight and then 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 in vacuo and dichloromethane was added to the residue. The organic phase was washed with 2N NaOH solution, saturated NaCl solution, dried over Na2SO4, and the solvent removed in vacuo. The residue was then chromatographed to give tert-butyl N-[4-(isopropylformylamino)cyclohexyl]methylcarbamate: 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).

Workup

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

Sources & evidence

ORD record
ord-571d13456ce04df79da058cc68545d19
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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