反応 #1563926

反応方程式

methyl 4-[(1S)-1-[[(2R)-piperidine-2-carbonyl]amino]ethyl]benzoate hydrochloride

2-(4-fluorophenoxy)acetaldehyde

acetic acid

sodium triacetoxyborohydride

→

title compound

収率 70.4%

methyl 4-[(1S)-1-[[(2R)-1-(2-(4-fluorophenoxy)ethyl)piperidine-2-carbonyl]amino]ethyl]benzoate

収率 70.4%

溶媒

DCE

反応条件

後処理

1. 1
   その他Quench
2. 2
   その他the reaction with saturated aqueous NaHCO3 (25 mL)
3. 3
   抽出extract the aqueous layer with EtOAc (2×25 mL)
4. 4
   洗浄Wash the combined organic layers with saturated aqueous NaCl (25 mL)
5. 5
   乾燥dry the organic phase over MgSO4
6. 6
   ろ過filter
7. 7
   濃縮concentrate under reduced pressure
8. 8
   洗浄eluting with a gradient of 0% to 100% EtOAc/hexanes
9. 9
   濃縮Concentrate the fractions
10. 10
    workup.ADDITIONcontaining the desired product under reduced pressure

実験手順

Stir a mixture of methyl 4-[(1S)-1-[[(2R)-piperidine-2-carbonyl]amino]ethyl]benzoate hydrochloride (650 mg, 1.99 mmol) and 2-(4-fluorophenoxy)acetaldehyde (337 mg, 2.19 mmol) in DCE (9.9 mL) at room temperature for 30 min. Add acetic acid (0.113 mL, 1.99 mmol) and sodium triacetoxyborohydride (590 mg, 2.78 mmol) and stir at room temperature for three days. Quench the reaction with saturated aqueous NaHCO3 (25 mL) and extract the aqueous layer with EtOAc (2×25 mL). Wash the combined organic layers with saturated aqueous NaCl (25 mL), then dry the organic phase over MgSO4, filter, and concentrate under reduced pressure. Subject the resulting oil to flash chromatography on silica gel, eluting with a gradient of 0% to 100% EtOAc/hexanes. Concentrate the fractions containing the desired product under reduced pressure to provide the title compound as a white solid (600 mg, 70% yield). Mass spectrum (m/z) 429 (M+H)+, 451 (M+Na)+.

出典