تفاعل #2446081

معادلة التفاعل

1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethyl-benzoate

formaldehyde

sodium triacetoxyborohydride

acetic acid

→

1-(cyclohexyl(methyl)amino)propan-2-yl-2,4,6-trimethylbenzoate

المذيبات

DCM

dioxane-HCl

ظروف التفاعل

المعالجة

1. 1
   أخرىSolvent was evaporated
2. 2
   workup.DISSOLUTIONCrude solid was dissolved in DCE (10 ml)
3. 3
   أخرىThe resultant reaction mixture
4. 4
   workup.STIRRINGwas stirred at rt for 16 hours
5. 5
   غسيلwashed with 1N NaOH, water and brine
6. 6
   تجفيفThe organic layer was dried over sodium sulphate
7. 7
   تركيزconcentrated to dryness
8. 8
   أخرىThe crude compound was purified by column chromatography

الإجراء التجريبي

1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethyl-benzoate (1.0 g, 2.48 mmol) was dissolved in dioxane-HCl (15 mL). The reaction mixture was stirred at rt for 2 hours. Solvent was evaporated. Crude solid was dissolved in DCE (10 ml) and formaldehyde (0.34 mL, 3.96 mmol), and sodium triacetoxyborohydride (1.67 g, 7.92 mmol) and acetic acid (0.5 mL) were added at 0° C. The resultant reaction mixture was stirred at rt for 16 hours. The reaction mixture was diluted in DCM and washed with 1N NaOH, water and brine. The organic layer was dried over sodium sulphate and concentrated to dryness. The crude compound was purified by column chromatography to obtain 1-(cyclohexyl(methyl)amino)propan-2-yl-2,4,6-trimethylbenzoate. Yield: 0.6 (76%); 1H NMR (400 MHz, CDCl3) δ 6.82 (s, 2 H), 5.27-5.25 (m, 1 H), 2.64-2.62 (m, 1 H), 2.51-2.46 (m, 1 H), 2.29 (s, 9 H), 2.25 (s, 3 H), 1.75-1.74 (m, 4 H), 1.33-1.31 (d, J=6 Hz, 3 H), 1.18-1.13 (m, 4 H), 1.09-1.03 (m, 1H); LCMS: m/z=317.8 [M+H], RT=2.98 min (Column: X, Program: P1).

المصدر