反応 #44768

反応方程式

1-Boc-2-aminomethylpiperidine

methyl 4-formylbenzoate

acetic acid

sodium triacetoxyborohydride

→

1,1-dimethylethyl 2-((4-(methoxycarbonyl)phenylmethylamino)methyl)-1-piperidinecarboxylate

収率 96.6%

溶媒

dichloroethane

water

反応条件

後処理

1. 1
   workup.ADDITIONwere added sequentially
2. 2
   抽出extracted with methylene chloride (2×)
3. 3
   乾燥The organic phase was dried over sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他Purification on silica gel using a gradient of ethyl acetate in hexane

実験手順

A solution of 1-Boc-2-aminomethylpiperidine (429 mg, 2 mmol) and methyl 4-formylbenzoate (329 mg, 2 mmol) in dichloroethane (10 mL) was stirred as acetic acid (180 mg, 3 mmol) and sodium triacetoxyborohydride (487 mg, 2.3 mmol) were added sequentially. The reaction was stirred at ambient temperature for 17 hours. The reaction was poured into water and extracted with methylene chloride (2×). The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification on silica gel using a gradient of ethyl acetate in hexane gave 0.7 g of 1,1-dimethylethyl 2-((4-(methoxycarbonyl)phenylmethylamino)methyl)-1-piperidinecarboxylate.

出典