反応 #2446081

反応方程式

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

溶媒

DCM

dioxane-HCl

反応条件

後処理

1. 1
   その他Solvent was evaporated
2. 2
   workup.DISSOLUTIONCrude solid was dissolved in DCE (10 ml)
3. 3
   その他The resultant reaction mixture
4. 4
   workup.STIRRINGwas stirred at rt for 16 hours
5. 5
   洗浄washed with 1N NaOH, water and brine
6. 6
   乾燥The organic layer was dried over sodium sulphate
7. 7
   濃縮concentrated to dryness
8. 8
   その他The crude compound was purified by column chromatography

実験手順

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).

出典