反応 #1153156

反応方程式

(2S,3S)-(−)-3-amino-2-phenylpiperidine

benzyl chloroformate

diisopropylethylamine

→

title compound

収率 80.2%

(2S,3S)-3-Benzyloxycarbonylamino-2-phenylpiperidine

収率 80.2%

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   その他quenched by addition of water
2. 2
   その他The mixture was separated
3. 3
   洗浄The organic layers were successively washed with a portion of brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   その他evaporated
6. 6
   その他The residue was purified by flash chromatography (5% methanol in methylene chloride)

実験手順

To a solution of (2S,3S)-(−)-3-amino-2-phenylpiperidine (152 mg, 0.86 mmole) (L-tartaric acid salt, [a]D=−57.1 (EtOH, c=0.1138)) in methylene chloride (10 mL) at room temperature was added benzyl chloroformate (0.123 mL, 0.86 mmole) and diisopropylethylamine (0.45 mL, 2.58 mmole). The reaction was stirred for 16 hours and was then diluted with methylene chloride and quenched by addition of water. The mixture was separated and the aqueous was reextracted with 2 additional aliquots of methylene chloride. The organic layers were successively washed with a portion of brine, dried over sodium sulfate, combined and evaporated. The residue was purified by flash chromatography (5% methanol in methylene chloride) to afford 214 mg (80%) of the title compound. NMR (CDCl3): δ 1.55 (br, d, J=9 Hz, 1 H), 1.6-1.9 (m, 2 H), 2.02 (br. d, J=9 Hz, 1 H), 2.79 (dd, J=9 and 10 Hz, 1 H), 3.22 (dd, J=1 and 10 Hz, 1 H), 3.91 (br. s, 1 H), 4.01 (dd, J=1 and 8 Hz, 1 H), 4.89 (s, 2 H), 5.65 and 5.88 (2 br. s, 1 H), 7.1-7.4 (m, 10 H).

出典