反応 #162189

反応方程式

(3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanone

29b

(S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanone

3-bromoprop-1-ene

NH4Cl

→

desired product

(3S)-1-allyl-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol

溶媒

DMF

反応条件

後処理

1. 1
   抽出extracted twice with EtOAc
2. 2
   洗浄The combined organic phases were washed twice with brine
3. 3
   乾燥dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The crude residue was purified by silica gel chromatography

実験手順

To a solution of (3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanone, 29b, (0.60 g, 2.46 mmol) and 3-bromoprop-1-ene (0.43 mL, 4.92 mmol) in DMF was added Zn dust (0.32 g, 4.92 mmol). The reaction was stirred at room temperature for 3 days. The mixture was diluted into aqueous saturated NH4Cl solution, extracted twice with EtOAc. The combined organic phases were washed twice with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography using 0-50% EtOAc/hexanes gradient to afford 553 mg of desired product, 58a, as an oil. LC/MS-two peaks corresponding to two diastereomeric products: 286.4 (M+H), RT=3.41 and 3.78.

出典