反応 #2033719

反応方程式

Intermediate 76

2-[1-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-yl]ethanol borane

triethylamine

Methanesulfonyl chloride

→

title compound

2-[1-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-yl]ethyl methanesulfonate borane

溶媒

Dichloromethane

反応条件

後処理

1. 1
   その他the cooling bath was removed
2. 2
   その他The solution was partitioned between aqueous ammonium chloride (200 ml) and DCM (200 ml)
3. 3
   その他The layers were separated
4. 4
   抽出the aqueous phase was further extracted with DCM (200 ml)
5. 5
   洗浄The combined organic extracts were washed with water (200 mL)
6. 6
   乾燥dried (Na2SO4)
7. 7
   ろ過filtered through a hydrophobic frit
8. 8
   その他evaporated in vacuo
9. 9
   その他The crude product was purified by column chromatography (silica, 0-25% Methanol in DCM)
10. 10
    濃縮concentrated

実験手順

A stirred suspension of Intermediate 76 (830 mg) in Dichloromethane (DCM) (40 mL), under nitrogen, was treated with triethylamine (0.501 mL) then cooled to ca. 0° C. (ice bath). Methanesulfonyl chloride (0.222 mL) was added via syringe, then the cooling bath was removed and stirring continued for 2 h. The solution was partitioned between aqueous ammonium chloride (200 ml) and DCM (200 ml). The layers were separated and the aqueous phase was further extracted with DCM (200 ml). The combined organic extracts were washed with water (200 mL), dried (Na2SO4), filtered through a hydrophobic frit and evaporated in vacuo. The crude product was purified by column chromatography (silica, 0-25% Methanol in DCM). The appropriate fractions were combined and concentrated to afford the title compound, 368 mg. LC/MS (M-BH2)-411/413, Rt 2.18 mins (5 min run, TFA modifier).

出典