Реакция #2446081

Уравнение реакции

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

Растворители

DCM

dioxane-HCl

Условия реакции

Обработка

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

Методика

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).

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