Tetrahydrofuran → tert-butyl N-[4-(isopropylformylamino)cyclohexyl]methylcarbamate
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
Procedure
A solution of a tert-butyl N-[4-(isopropylamino)-cyclohexyl]methylcarbamate (7.89 mmol, 1 equivalent) in THF (5 ml) was added dropwise to a solution of 1H-benzotriazole-1-carboxaldehyde (8.68 mmol, 1.2 equivalent) in THF (10 ml) at room temperature, stirred overnight and heated at reflux temperature for two hours. 1H-Benzotriazole-1-carboxaldehyde (1 equivalent) was added and stirred overnight. The solvent was removed and dichloromethane was added to the residue. The organic extract was washed with 2N NaOH solution, washed with saturated NaCl solution, and dried over Na2SO4. The solvent was then removed and the product 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
- temperatureheated
- temperatureat reflux temperature for two hours
- stirringstirred overnight
- customThe solvent was removed
- additiondichloromethane was added to the residue
- extractionThe organic extract
- washwas washed with 2N NaOH solution
- washwashed with saturated NaCl solution
- dry with materialdried over Na2SO4
- customThe solvent was then removed
- customthe product chromatographed
Sources & evidence
- ORD record
- ord-bd9722d2a93447d8995758ab4f1934af
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124331
Reaction notes
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